Month: August 2021

Adding a certain compound to certain chemical reactions, such as: 612-55-5, name is 2-Iodonaphthalene, 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 612-55-5, Recommanded Product: 612-55-5

General procedure: A 100mL flask was charged with Pd(PPh3)Cl2 (70 mg, 0.1 mmol) and CuI (38 mg, 0.2 mmol). After the flask was evacuated and refilled with argon, NEt3 (20 mL) was added and the suspension was stirred at room temperature. A solution of iodobenzene (10a, 2.04 g, 10 mmol) and propargyl alcohol (616 mg, 11 mmol) in NEt3 (10 mL) was added to the suspension. After the reaction was complete (monitored by TLC), the mixture was filtered through a plug of Celite and washed with EtOAc (20 mL x 3). The combined solution was concentrated and purified by column chromatography on silica gel (Hexane/EtOAc 3:1, v/v) to afford 3-phenylprop-2-yn-1-ol (11a, 1.24 g, 94% yield) as a yellow oil.

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:
Article; Xu, Bin; Gartman, Jackson A.; Tambar, Uttam K.; Tetrahedron; vol. 73; 29; (2017); p. 4150 – 4159;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 628-77-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 628-77-3 name is 1,5-Diiodopentane, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Diiodopentane (0.63 mL, 4.21 mmol, 5 eq) and potassium carbonate (116 mg, 0.84 mmol, Ieq) were added to a solution of phenol 64 (400 mg, 0.84 mmol) in acetone (4 mL, dried overmolecular sieves). The reaction mixture was then warmed to 60C and stirred for 6 hours. Acetone was removed by rotary evaporation under reduced pressure. The resulting residue was subjected to flash column chromatography (silica gel; 50/50, v/v, hexane/ethyl acetate,). Pure fractions were collected and combined and excess eluent was removed to provide 15in 90% yield. LC/MS, 3.90 mm (ES+) m/z (relative intensity)670.91 ([M], 100). 1H NMR (400MHz, CDCI3) 5 7.23 (s, I H), 6.69 (s, I H), 6.60 (s, I H), 5.87 (d, J = 8.8 Hz, I H), 5.83 – 5.68(m, J = 5.6 Hz, I H), 5.15 – 5.01 (m, 2H), 4.67 -4.58 (m, I H), 4.45 – 4.35 (m, I H), 4.04 – 3.93(m, 2H), 3.91 (s, 3H), 3.73 (td, J= 10.0, 3.8 Hz, IH), 3.25-3.14 (m, J= 8.5, 7.0 Hz,2H), 2.92 (dd, J= 16.8, 10.3 Hz, IH), 2.38 (d, J= 16.8 Hz, IH), 1.95-1.81 (m, 4H), 1.77 (s,3H), 1.64-1.49 (m, 2H), 0.88 (s, 9H), 0.25 (s, 3H), 0.23 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,5-Diiodopentane, and friends who are interested can also refer to it.

Reference:
Patent; SPIROGEN SARL; ADC THERAPEUTICS SARL; HOWARD, Philip Wilson; VAN BERKEL, Patricius, Hendrikus, Cornelis; WO2015/52535; (2015); A1;; ; Patent; SPIROGEN SARL; ADC THERAPEUTICS SARL; HOWARD, Philip Wilson; VAN BERKEL, Patricius Hendrikus Cornelis; WO2015/52534; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 181765-86-6,Some common heterocyclic compound, 181765-86-6, name is Methyl 5-bromo-2-iodobenzoate, molecular formula is C8H6BrIO2, 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.

500mL round-bottom flask reactor, methyl 5-bromo-2-iodo benzoate (25.0g, 73mmol) in 4-dibenzofuran boronic acid [0410] (18.7g, 88mmol), tetrakis (triphenylphosphine) palladium (1.7g, 0.15mmol), potassium carbonate (20.2 g, 146.7mmol) put the toluene 125 mL, tetrahydrofuran 125mL, water 50 mL. The temperature of the reactor was 80 C, 10 hours was stirred. When the reaction is complete cool down the temperature of the reactor to room temperature, extracted with ethyl acetate and the organic layer was separated It was. The organic layer was concentrated under reduced pressure and separated by column chromatography to give the intermediate 1-a. (75.0g, 60.1%)

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

Reference:
Patent; SFC CO LTD; PARK, SEOK BAE; SONG, JU MAN; LEE, YUR IM; KIM, HEE DAE; PARK, SANG WOO; JEONG, KYUNG SEOK; CHA, SOON WOOK; (96 pag.)KR2015/130206; (2015); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

33348-34-4, name is 4-Amino-3-iodobenzonitrile, 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. name: 4-Amino-3-iodobenzonitrile

Preparation 52; 6-Cyano-2,3,4,9-tetrahydro-lH-carbazol-3-yl)-carbamic acid tert-butyl esterAs described in C Chen et al, J. Org. Chem. (1997) 62, 2676-2677, mix 3- iodo-4-aminobenzonitrile (T. H. Jonckers, et al, J. Med. Chem. 45 (16) 3497-3508 (2002)) (1.3 g, 5.3 mmol) and (4-oxo-cyclohexyl)-carbamic acid tert-butyl ester (3.4 g, 16 mmol) l,4-diazobicyclo[2.2.2]octane (DABCO)(1.8 g, 16 mmol), magnesium sulfate (960 mg, 8 mmol) and DMF (30 mL). Sparge the stirred mixture with nitrogen for 10 min and add palladium(II) acetate (58 mg, 0.26 mmol) and place in a 105 C pre-heated oil bath. After 18 h, cool and dilute with EtOAc. Gravity filter the reaction into a separatory funnel and shake with water/EtOAc. Dry the organic layer (MgSO4) and concentrate to give a dark brown oil. Triturate with hexane (insoluble material is starting ketone). Concentrate the hexane solution and purify by silica gel chromatography (120 g), eluting with methylene chloride (0-40 min), then 10% EtOAc/methylene chloride (40-70 min) to give 550 mg (33%) of an off- white foam. MS (ES): m/z 312 (M+l), 310 (M-I); HPLC: R1 = 2.30 min, (97%).

The synthetic route of 33348-34-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2007/2181; (2007); A2;,
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

Application of 2043-57-4,Some common heterocyclic compound, 2043-57-4, name is 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane, molecular formula is C8H4F13I, 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.

1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluoro-8-iodooctane (30.8 g, 65 mmol) was dissolved in a mixture of pentane (180 mL) and diethyl ether (120 mL) The solution was stirred and cooled to -78 C before addition of 1.6 M t-butyllithium in hexane (45 mL, 72 mmol). After stirring for 15 min at this temperature freshly distilled trichloromethylsilane (2.75 g, 18.4 mmol) was added. The mixture was stirred for further 2 h at -78 C and then 1 h at 0 C, thereafter it was poured onto ice with stirring for 15 min. The resulting biphasic mixture was filtered through silica gel. The layers were separated and the aqueous phase was extracted with diethyl ether (3* 50 mL). The combined organic phases were dried (MgSO4) and solvents evaporated in vacuum to afford a yellow oil (17.2 g, 16 mmol, 85%). 1H NMR delta = 0.18 (s, 3H, SiCH3), 0.91 (m, 6H, SiCH2CH2CF2), 2.07 (m, 6H, CH2CF2). 13C {1H} NMR delta = -6.59 (s, SiCH3), 2.59 (s, SiCH2), 25.54 (t, 2JCF = 24.0 Hz, CH2CF2), 106.80-125.18 (m, CF3, CF2). 19F NMR delta = -127.13 (m, 6F, CF2), -124.17 (m, 6F, CF2), -123.77 (m, 6F, CF2), -122.78 (m, 6F, CF2), -117.07 (m, 6F, CF2), -81.99 (t, 9F, 3JHH = 10.1 Hz, CF3). 29Si {1H} NMR delta = 7.06.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane, its application will become more common.

Reference:
Article; Stra?ak, Toma?; ?t’astna, Lucie ?ervenkova; Bilkova, Veronika; Skoupa, Veronika; Karban, Jind?ich; Cu?inova, Petra; ?ermak, Jan; Journal of Fluorine Chemistry; vol. 178; (2015); p. 23 – 29;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 52548-14-8, 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. 52548-14-8, name is 2-Iodo-5-methylbenzoic acid belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step B: Methyl 2-iodo-5-methyl-benzoate The compound of the above Step (6.25 g, 23.9 mmol) is dissolved in anhydrous methanol (100 mL), and then SOCl2 (3.6 mL, 49 mmol) is added dropwise to the well-stirred solution. The solution is refluxed for 18 hours and then evaporated to a volume of 25 mL and then poured into crushed ice (100 g). The resulting mixture is extracted with diethyl ether (2*75 mL). The organic phase is washed with saturated aqueous NaHCO3 solution and then brine, dried over Na2SO4 and evaporated to dryness to yield the title compound.

The synthetic route of 2-Iodo-5-methylbenzoic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LE TIRAN, Arnaud; LE DIGUARHER, Thierry; STARCK, Jerome-Benoit; HENLIN, Jean-Michel; GUILLOUZIC, Anne-Francoise; DE NANTEUIL, Guillaume; GENESTE, Olivier; FEJES, Imre; TATAI, Janos; NYERGES, Miklos; DAVIDSON, James Edward Paul; MURRAY, James Brooke; CHEN, I-Jen; DURAND, Didier; US2015/31673; (2015); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 2142-70-3, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 2142-70-3 as follows.

A solution of 1-(2-iodophenyl)ethanone (0.86g, 3.49mmol) in THF (l5mL) was treated with trimethylphenylammonium tribromide (1.31g, 3.49mmol) in small portions over 10 minutes at R.T. The resulting yellow suspension was stirred at R.T. for 2 hours. A whiteprecipitate formed and was filtered, washed with diethyl ether and the filtrate was concentrated under reduced pressure to give the crude product. The product was purified by silica column chromatography using Combiflash RF automated purification system (0-100% EtOAc – hexane gradient elution) to give title compound as a yellow oil. The oil was confirmed as desired product by 1H NMR (500MHz ODd3) O 7.97(1 H, d, J=11Hz, ArH), 7.47(2 H, d, J= 8Hz, ArH), 7.18-7.22(1 H, m, J= 4, 12Hz, ArH), 4.47(2 H, 5, CH2Br).

According to the analysis of related databases, 2142-70-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF DUNDEE; SMITH, Alasdair; HUGGETT, Margaret Jean; SPINKS, Daniel; WOODLAND, Andrew; GILBERT, Ian Hugh; (156 pag.)WO2016/132134; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

618-91-7, name is Methyl 3-iodobenzoate, 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. Recommanded Product: 618-91-7

To a 100-ml autoclave, were added aryl iodide (1.0 mmol),acylhydrazine (2.0 mmol), the catalyst (Pd: 0.78 mol%), base(1.06 mmol) and DMSO (5.0 ml). The autoclave was flushed by CO flow and pressurized to 4.0 MPa. The reaction was performed at 120C for the given time. The reaction mixture was extracted with ethyl acetate. The carbonylation product was obtained by purifica-tion over silica column with the eluent of ethyl acetate/petroleumether (60-90C) (v/v, 2:1). In the five-run recycling test, the cata-lyst was separated by adding 30 ml mixture of petroleum ether anddiethyl ether and washed by ethyl acetate and diethyl ether afte reach testing run. The catalyst was dried vacuum and then recycled into the next batch.

The synthetic route of 618-91-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Bingfeng; Li, Fengbo; Huang, Zhijun; Lu, Tao; Yuan, Guoqing; Applied Catalysis A: General; vol. 481; (2014); p. 54 – 63;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 39998-81-7, These common heterocyclic compound, 39998-81-7, name is 2-Fluoro-4-iodo-1-methylbenzene, 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.

2-Fluoro-4-iodobenzoic acid (Compound B) A round bottom (RB) flask containing a solution of 8.0 g (27.0 mmol) of sodium dichromate in 44 mL of glacial acetic acid was placed in an external water bath (21 C.) and left exposed to air. To the resultant orange slurry was added 3.2 g (13.6 mmol) of 2-fluoro-4-iodotoluene followed by the dropwise addition of 22 mL of c. sulfuric acid via syringe (caution: if added too quickly there is a tendency for the mixture to erupt). After the addition of approximately 8 mL of sulfuric acid, a green solid precipitated and the water bath temperature had risen (25 C.). The green reaction mixture was heated in an oil bath (90 C.) for one hour, allowed to cool to ambient temperature, diluted with 1N NaOH solution (aq.) and ethyl acetate (500 mL) and then quenched with sat. NaHCO3 (aq.) solution. The organic phase was separated and washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo to an orange oil. Residual acetic acid was removed by further extraction between ethyl acetate and sat. NaHCO3 (aq.) solution and washing of the organic phase with water and brine. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to give the title compound as an orange solid. PMR (DMSO-d6): delta 7.61 (1H, t, J=8.0 Hz, J (C-F)=8.0 Hz), 7.67 (1H, dd, J=1.5, 8.2 Hz), 7.78 (1H, dd, J=1.5 Hz, J (C-F)=8.9 Hz).

The synthetic route of 39998-81-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Allergan Sales, Inc.; US6037488; (2000); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com