Category: 116632-39-4

116632-39-4, A common compound: 116632-39-4, name is 5-Bromo-2-iodotoluene, belongs to iodides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

General procedure: To a 20 mL vial with a stir bar was added aryl halide 1 (2.00 mmol), Pd(dba)2 (28.8 mg, 2.5 mol %), Xantphos (28.9 mg, 2.5 mol %). The vial was sealed with a Teflon-lined cap and THF (6.0 mL) was added. The mixture was vacuumed and backfilled with nitrogen (3×). A solution of ethyl 2-bromozincacetate (2a) in THF (0.40 M, 6.0 mL, 1.2 equiv) filtered through a Target Nylon 0.45 mum filter (1.25-inch OD) was syringed in and the reaction mixture was then heated to 65 C and monitored by HPLC. Upon reaction completion based on HPLC analysis (?95% conversion unless the reaction was stalled), the mixture was cooled to room temperature and quenched with 1 M aq HCl (5.0 mL), followed by addition of brine (5.0 mL). The organic layer was separated and concentrated in vacuum. The residue was purified by silica gel column chromatography using gradient EtOAc in hexanes.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-Bromo-2-iodotoluene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wong, Brian; Linghu, Xin; Crawford, James J.; Drobnick, Joy; Lee, Wendy; Zhang, Haiming; Tetrahedron; vol. 70; 7; (2014); p. 1508 – 1515;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 116632-39-4, name is 5-Bromo-2-iodotoluene, molecular formula is C7H6BrI, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Recommanded Product: 116632-39-4

Apparatus set-up: (0305) A 5 L 3 -necked round-bottomed flask, equipped with a mechanical overhead stirrer, reflux condenser, nitrogen inlet and exhaust. (0306) Experimental Procedure: (0307) Intermediate 3 (128 g, 0.435 mol) and intermediate 4 (128.8 g, 0.435 mol) were taken in toluene (1 L) and ethanol (1 L). (0308) Sodium carbonate solution (161.3 g, 1.522 mol, dissolved in 500 mL of water) was added. (0309) The reaction mixture was degassed with nitrogen for an hour. (0310) PdCl2 (PPh3)2 (15.2 g, 0.021 mol) was added and heated at 80 C for 18 h. (0311) After completion of the reaction, the mixture was filtered through a Florosil-silica plug and concentrated. (0312) The residue was dissolved in ethyl acetate (2 L), washed with water (1 L), brine (1 L), dried over sodium sulphate and concentrated. (0313) The crude product (159 g) was purified by silica column chromatography using 5 to 6 % ethyl acetate in hexane as an eluent to get 65 g of Intermediate B with 81 % HPLC purity. It was again purified by reverse phase column chromatography (in 5 g per run) using water/ acetonitrile as an eluent to get 35.6 g of Intermediate B. (0314) The material was dissolved in dichloromethane (500 mL), heated to 45 C, filtered the hot solution and concentrated to get 35 g of Intermediate B with 99.64 % HPLC purity as viscous oil. (0315) ^-NMR (400 MHz, COCh): delta [ppm] 2.29 (s, 3H), 7.19 (d, = 8.0 Hz, 1H), 7.37 – 7.42 (m, 3H), 7.47 – 7.52 (m, 2H), 7.61 (d, / = 8.4 Hz, 2H), 7.86 (s, 1H), 7.96 (d, = 7.6 Hz, (0316) 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 116632-39-4, its application will become more common.

Reference:
Patent; CAMBRIDGE DISPLAY TECHNOLOGY LIMITED; SUMITOMO CHEMICAL CO., LTD; HUMPHRIES, Martin; TARRAN, William; KAMTEKAR, Kiran; STACKHOUSE, Philip; LEE, James; (76 pag.)WO2017/153731; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 116632-39-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 116632-39-4, name is 5-Bromo-2-iodotoluene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Standard procedure: Into a flask of 150 mL of EtiO at -78 C under N2, 4-bromo-1-iodo-2-methylbenzene (22.6 g, 76.1 mmol) in anhydrous EtiO (10 mL) is added.. Then n-BuLi in hexanes (2.5 M, 26 mL, 65 mmol) is added dropwise at -78 C and stirred for an additional hour. Then, freshly prepared crude (2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6- ((benzyloxy)methyl)tetrahydro-2H-pyran-2-carbaldehyde (12.0 g, 21.7 mmol) dissolved in E20 (90 mL) is added via cannula over a period of 5 minutes. The mixture is stirred at -78 C for 30 min, and then slowly warmed to 0 C over a period of 1.5 h. The reaction mixture is quenched with saturated aq. NLLCl and extracted with EtOAc (250 mL x 3). The combined organic phase is washed with brine (100 mL), dried over NaiSOr and filtered. The filtrate is concentrated under reduced pressure and the residue is purified by silica gel chromatography DCM/EtO Ac/petroleum ether to give (R)-(4-bromo-2-methylphenyl)((2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methanol (4.0 g, 25% yield for two steps) as a light yellow oil and (S)-(4-bromo-2-methylphenyl)((2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methanol (8.0 g, 51 % yield for two steps) as a light yellow oil. (R) isomer: Formula: C42H43Br06 Exact Mass: 722.22 Molecular Weight: 723.69 Analytical data for 1 R: NMK (300 MHz, CDCl3) d 7.41-7.28 (m, 21H), 7.18-7.13 (m, 2H), 5.08 (d,.7= 5.1Hz, 1H), 4.71 (d, J= 11.7 Hz, 1H), 4.64-4.56 (m, 3H), 4.49 (s, 2H), 4.40 (s, 2H), 4.28 – 4.21 (m, 1H), 4.18 – 4.13 (m, 1H), 4.10 (t, J= 5.1Hz, 1H), 3.99-3.94 (m, 1H), 3.89 (t, J= 5.9 Hz, 1H), 3.83-3.70 (m, 2H), 3.49 (br. s., 1H), 2.29 (s, 3H). ESI-MS [M+Na+] calcd for (CriH-nB ENa) found: 745.5 (100%), 747.5 (97.3%) (S) isomer: Formula: C42H43BrC>6 Exact Mass: 722.22 Molecular Weight: 723.69 Analytical data for IS: 1H NMR (300 MHz, CDCl3) d 7.37 – 7.16 (m, 23H), 5.06 (d, J= 5.5 Hz, 1H), 4.73 – 4.67 (m, 1H), 4.62 – 4.44 (m, 7H), 4.11 – 4.03 (m, 2H), 3.85 – 3.76 (m, 3H), 3.73 – 3.67 (m, 2H), 3.19 (br. s., 1H), 2.18 (s, 3H). ESI-MS [M+Na]+ calcd for C42H43BrOeNa+ 745.21, found 745.5 (100%), 747.5 (97.3%).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-Bromo-2-iodotoluene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; FIMBRION THERAPEUTICS, INC.; BISHOP, Michael Joseph; COLANDREA, Vincent J.; LI, Yuehu; STEWART, Eugene L.; STRAMBEANU, Iulia; WIDDOWSON, Katherine Louisa; JANETKA, James Walter; MCGRANE, Laurel Kathryn; (0 pag.)WO2020/12336; (2020); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 116632-39-4, name is 5-Bromo-2-iodotoluene, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 116632-39-4, HPLC of Formula: C7H6BrI

sec-BuLi (1.4M in cyclohexane, 137.4 ml, 192.4mmol) was added dropwise to a suspension of (2,8-dibenzothiophenediyl)bis-9H,9’H-carbazole (82.5 g, 160.3 mmol)in tetrahydrofuran (1650 ml) at -74 C. After stirring at -40C. for 4 hours, the reaction mixture was re-cooled to -74 o C.and isopropoxyboronic acid, pinacol ester ( 45.8 ml, 224.4mmol) was added dropwise and the mixture allowed towarm to room temperature over night. It was then cooled to-30 C., quenched by the dropwise addition of HCl (2M indiethylether, 88.2 ml, 176.3 mmol), warmed to ambienttemperature and concentrated under reduced pressure. Theresulting precipitate was removed and the filtrate concentratedunder reduced pressure and recrystallized (once fromhexane:toluene and twice from acetonitrile:toluene) to give(A) as a white solid (49.6 g, 48% yield) after drying at 50C. under vacuumHPLC: 95.88%.[0126] 1H-NMR (600 MHz, CDC13 ):delta H [ppm] 1.47 (s,12H), 7.28 (m, 4H), 7.40 (m, 8H), 7.70 (dd, 1=1.9 Hz, 8.5Hz, lH), 8.15 (m, 6H), 8.29 (d, 1=1.7 Hz, lH), 8.38 (d, 1=2.0Hz, lH).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Cambridge Display Technology Limited; Sumitomo Chemical Company Limited; Steudel, Annette; Bourcet, Florence; (29 pag.)US2018/342684; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 116632-39-4, name is 5-Bromo-2-iodotoluene, molecular formula is C7H6BrI, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. category: iodides-buliding-blocks

General procedure: (R)-(4-bromo-2-methylphenyl)((2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6- ((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methanol (101R) and (S)-(4-bromo-2- methylphenyl)((2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6- ((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methanol (101S). Synthesis B: Into a flask containing 4-bromo-1-iodo-2-methylbenzene (22.6 g, 76.1 mmol) in anhydrous Et2O (200 mL) under N2, was added n-BuLi/Hexanes (2.5 M, 26 mL, 65.23 mmol) dropwise at -78 C. After 1 h, the freshly prepared crude 2,3,4,6-Tetra-O-benzyl-alpha-D-mannopyranosyl carbaldehyde (12.0 g, 21.74 mmol) dissolved in Et2O (90 mL) was added via cannula over a period of 5 minutes. The mixture was stirred at -78 C for 30 min, and then slowly warmed to 0 C over a period of 1.5 h. The reaction mixture was quenched with saturated aq. NH4Cl and extracted with EtOAc (250 mL x 3). The combined organic phase was washed with brine (100 mL), dried over Na2SO4 and filtered .The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography (phase A: PE, phase B: CH2Cl2 / EtOAc / PE (20/1/2)) to give the 101R (4.0 g, 26% yield for two steps) as light yellow oil and 101S (8.0 g, 51% yield for two steps) as light yellow oil. Formula: C42H43BrO6 Exact Mass: 722.22 Molecular Weight: 723.69 Analytical data for Intermediate 101R: 1H NMR (300 MHz, CDCl3) delta 7.41-7.28 (m, 21H), 7.18-7.13 (m, 2H), 5.08 (d, J = 5.1 Hz, 1H), 4.71(2d, J = 11.7 Hz, 1H), 4.64-4.56 (m, 3H), 4.49 (s, 2H), 4.40 (s, 2H), 4.28 – 4.21(2m, 1H), 4.18 – 4.13 (m, 1H), 4.10 (t, J = 5.1 Hz, 1H), 3.99-3.94 (m, 1H), 3.89 (t, J = 5.9 Hz, 1H), 3.83-3.70 (m, 2H), 3.49 (br. s., 1H), 2.29 (s, 3H). ESI-MS [M+Na+] calcd for (C42H43BrO6Na) found: 745.5 (100%), 747.5 (97.3%). Formula: C42H43BrO6 Exact Mass: 722.22 Molecular Weight: 723.69 Analytical data for Intermediate 101S: 1H NMR (300 MHz, CDCl3) delta 7.37 – 7.16 (m, 23H), 5.06 (d, J=5.5 Hz, 1H), 4.73 – 4.67 (m, 1H), 4.62 – 4.44 (m, 7H), 4.11 – 4.03 (m, 2H), 3.85 – 3.76 (m, 3H), 3.73 – 3.67 (m, 2H), 3.19 (br. s., 1H), 2.18 (s, 3H). ESI-MS [M+Na]+ calcd for C42H43BrO6Na+ 745.21, found 745.5 (100%), 747.5 (97.3%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 116632-39-4, its application will become more common.

Reference:
Patent; FIMBRION THERAPEUTICS, INC.; JANETKA, James, W.; MYDOCK-MCGRANE, Laurel; (136 pag.)WO2017/156508; (2017); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 116632-39-4,Some common heterocyclic compound, 116632-39-4, name is 5-Bromo-2-iodotoluene, molecular formula is C7H6BrI, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: To a stirred solution of 6-bromo-3-pyridyl boronic acid (1.25 equiv, 847 mg, 4.20 mmol) in 1,4-dioxane (30 mL) under nitrogen were added 5-bromo-2-iodotoluene (1 g, 3.36 mmol) and tetrakis-(triphenylphosphine)palladium(0) (0.05 equiv, 195 mg, 0.17 mmol). After 5 min of stirring, aqueous Na2CO3 (2.5 equiv, 892 mg, 8.42 mmol) in 5 mL of water was added. Then the mixture was heated to 80 C until the starting material was consumed (TLC). After cooling down to room temperature, the mixture was filtered on Celite and washed with CH2Cl2. The aqueous layer was extracted with EtOAc (2×50 mL). Combined organic layers were washed with saturated aqueous solution of NaCl (50 mL), and dried over MgSO4. Solvent was removed in vacuo and crude product was purified by column chromatography, with 99:1 cyclohexane/EtOAc affording 3c as a white solid (520 mg, 47%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-2-iodotoluene, its application will become more common.

Reference:
Article; Perato, Serge; Voisin-Chiret, Anne Sophie; Sopkova-De Oliveira Santos, Jana; Legay, Remi; Oulyadi, Hassan; Rault, Sylvain; Tetrahedron; vol. 68; 7; (2012); p. 1910 – 1917;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 116632-39-4, name is 5-Bromo-2-iodotoluene, belongs to iodides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 116632-39-4, Recommanded Product: 116632-39-4

Compound Kl 09 can be synthesized by a person of ordinary skill following Scheme 2 illustrated in FIG. 3. In the first step, compound S2-1 (available for purchase from Acros Organics, CAS No. 86-74-8) is combined with compound S2-2 (available for purchase from Alfa Aesar, CAS No. 116632-39-4), K2C03, and Cul in toluene at 80 C to form compound S2-3, In the second step, compound S2-3 is added to hexanes and cooled to 0 C before dropwise addition of nBuLi, followed by addition of B(OMe)3. The reaction can be allowed to stir before being quenched with aqueous HCl to form compound S2-4. In the third step, compound S2-4 is combined with compound S2-5 (available for purchase from Alfa Aesar, CAS No. 3842-55-5), Pd(OAc)2 and K3P04 in THF at 45 C for 24 hours to form compound Kl 09. It is understood that steps 1 , 2, and 3 can be performed and optimized by a person having ordinary skill in the art without undue experimentation.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-2-iodotoluene, and friends who are interested can also refer to it.

Reference:
Patent; Harvard College Dean Deng; A ·asipulu-gujike; R ·gemaisi-bomubaleierli; T ·D·xiseer; J ·akuileila-aipalakuilei; R ·P·yadangsi; D ·maikelaolin; D ·K·duweinade; (333 pag.)CN106661001; (2017); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 116632-39-4, These common heterocyclic compound, 116632-39-4, name is 5-Bromo-2-iodotoluene, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

(1) 4-Bromo-4′-fluoro-2-methylbiphenyl 4-Bromo-1-iodo-2-methylbenzene (10.5 g, 35.4 mmol) was dissolved in 1,2-dimethoxyethane (100 mL), and (4-fluorophenyl)boronic acid (7.4 g, 52.9 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium dichloride-dichloromethane adduct (1.5 g, 1.84 mmol) and potassium phosphate hydrate (18.8 g, 88.6 mmol) were added, followed by stirring at room temperature for 16 hours under a nitrogen atmosphere. After the insoluble materials in the reaction solution were filtered off, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (Moritex Corporation, elution solvent:hexane), and a fraction corresponding to the Rf value=0.60 (hexane) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (5.1 g, 19.2 mmol) as a colorless oil (yield 54%). 1H-NMR (500 MHz, CDCl3) delta: 7.42 (1H, s), 7.36 (1H, d, J=8 Hz), 7.27-7.21 (2H, m), 7.13-7.04 (3H, m), 2.22 (3H, s).

The synthetic route of 116632-39-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DAIICHI SANKYO COMPANY, LIMITED; US2011/112103; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 116632-39-4, These common heterocyclic compound, 116632-39-4, name is 5-Bromo-2-iodotoluene, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

(1) 4-Bromo-4′-fluoro-2-methylbiphenyl 4-Bromo-1-iodo-2-methylbenzene (10.5 g, 35.4 mmol) was dissolved in 1,2-dimethoxyethane (100 mL), and (4-fluorophenyl)boronic acid (7.4 g, 52.9 mmol), [1,1′-bis(diphenylphosphino)ferrocene]palladium dichloride-dichloromethane adduct (1.5 g, 1.84 mmol) and potassium phosphate hydrate (18.8 g, 88.6 mmol) were added, followed by stirring at room temperature for 16 hours under a nitrogen atmosphere. After the insoluble materials in the reaction solution were filtered off, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (Moritex Corporation, elution solvent:hexane), and a fraction corresponding to the Rf value=0.60 (hexane) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (5.1 g, 19.2 mmol) as a colorless oil (yield 54%). 1H-NMR (500 MHz, CDCl3) delta: 7.42 (1H, s), 7.36 (1H, d, J=8 Hz), 7.27-7.21 (2H, m), 7.13-7.04 (3H, m), 2.22 (3H, s).

The synthetic route of 116632-39-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DAIICHI SANKYO COMPANY, LIMITED; US2011/112103; (2011); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

116632-39-4, name is 5-Bromo-2-iodotoluene, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C7H6BrI

5-bromo-l-(bromomethyl)-2-iodobenzene (15a). A solution of 5-bromo-2- iodotoluene (6.75 g, 22.7 mmol) and 1,2-dichlorethane (25 mL) was stirred at room temperature in a 50 mL two neck round bottom under nitrogen. Benzoyl peroxide (281 mg, 1.14 mmol) and NBS (4.5 g, 25 mmol) were added at once and the resulting mixture was heated to reflux and irradiated with a 250 W incandescent flood lamp (12 in away from round bottom) for 5 h. The reaction mixture was allowed to cool to room temperature after which precipitates were filtered off and rinsed with hexane. The filtrate was dried with MgS04, filtered and the solvent removed under reduced pressure to provide an orange solid that was then rinsed with cold methanol yielding 3.99 g (10.6 mmol, 47%) of an off-white solid that was used without further purification. Characterization data matched that found in literature. Amijs, C. H. M, et al, Green Chem. 2003, 5, 470-474.

The synthetic route of 116632-39-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE JOHNS HOPKINS UNIVERSITY; TOVAR, John Dayton; CARUSO, Jr., Anthony; WO2011/127383; (2011); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com