Month: October 2020

2265-93-2, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 2265-93-2, name is 2,4-Difluoroiodobenzene, A new synthetic method of this compound is introduced below.

To toluene 3.0mL solution of tert-butyl 2-amino-4-phenethyl benzoate 0.10g were added 2,4-difluoro-1-iodobenzene 0.10mL, cesium carbonate 0.22g, tris(dibenzylideneacetone)dipalladium(0) 3mg and 2-dicyclohexylphosphino-2′,4′,6′-triisopropyl biphenyl 8mg, and it was stirred at 110C for 24 hours. After the reaction mixture was cooled to room temperature, tris(dibenzylideneacetone)dipalladium(0) 3mg and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 8mg were added to it, and it was stirred at 110C for 24 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 10% citric acid aqueous solution were added to it. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate:acetic acid=20:1:1] to give tert-butyl 2-(2,4-difluoroanilino)-4-phenethylbenzoate. Trifluoroacetic acid 10mL was added to the obtained tert-butyl 2-(2,4-difluoroanilino)-4-phenethylbenzoate, and it was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure, methanol was added to the obtained residue, and solid matter was filtrated to give 2-(2,4-difluoroanilino)-4-phenethylbenzoic acid 59mg of white solid. 1H-NMR(DMSO-d6) delta value: 2.82(4H,s),6.65(1H,s),6.70(1H,dd,J=8.1,1.5Hz),7.05(1H,t dd,J=8.6,2.8,1.3Hz),7.14-7.21(3H,m),7.23-7.30(3H,m),7.37(1H,ddd,J=11.1,8.9,2.8Hz),7.81(1H,d,J=8. 1Hz),9.46(1H,s),12.85-13.20(1H,broad).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; TOYAMA CHEMICAL CO., LTD.; EP1860098; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

A common heterocyclic compound, 1878-94-0, name is 2-(4-Iodophenoxy)acetic acid, molecular formula is C8H7IO3, 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. 1878-94-0.

The reaction mixture of N-deacetylthiocolchicine (24 mg, 0.064 mmol), 4-iodophenoxyacetic acid (41 mg, 0.15 mmol), EDCI (29 mg), DMAP (2 mg, 0.2 mmol) and dichloromethane (3 ml) was stirred at room temperature for 20 h. Then dichloromethane (20 ml) was added. Organic layer was washed with H2O, 5% Na2CO3 and brine, and then dried over MgSO4. After the solvent was removed under vacuum, the residue was separated by column chromatography (eluent: ethyl acetate and petroleum ether) to afford 35 mg N-Deacetyl-N-(4-iodophenoxyacetyl)thiocolchicine. [0571] The chemical structure analysis was performed by 1HNMR (CDCl3, 600 MHz).

The synthetic route of 2-(4-Iodophenoxy)acetic acid has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yang, Li-Xi; US2004/204370; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

628-21-7, These common heterocyclic compound, 628-21-7, name is 1,4-Diiodobutane, 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.

In three 250ml flask anthrone 19.4g (0.1mol), 150ml dried THF, was added with stirring diiodobutane (34.1g, 0.11mol), potassium tert-butoxide and 26.8g (0.24mol), the reaction was stirred for 3 hours at room temperature, the reaction was refluxed for 3 hours. Saturated ammonium chloride solution was added to quench the reaction, extracted with ethyl acetate, dried liquid separation, column chromatography to obtain 13.6 g of a white solid, a yield of 55%.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 628-21-7.

Reference:
Patent; KUNSHAN VISIONOX DISPLAY CO., LTD.; BEIJING VISIONOX TECHNOLOGY CO., LTD; Tsinghua University; Qiu, Yong; Fan, Hongtao; Duan, Lian; (49 pag.)CN103172524; (2016); B;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

112671-42-8, Name is 4-Bromo-1-iodo-2-nitrobenzene, 112671-42-8, 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.

(1) Take (100mmol) N-phenylcarbazole-1-boronic acid,32.6g (100mmol) of 2-iodo-5-bromonitrobenzene,(1%) Pd (PPh3) 4,40g (300mmol) sodium carbonate,Toluene (800mL),Ethanol (200 mL) and water (200 mL),Heated to reflux, reacted for 8h, the reaction was completed;The reaction solution was extracted with ethyl acetate, and the organic phase was concentrated.A yellow solid A was obtained;

Statistics shows that 4-Bromo-1-iodo-2-nitrobenzene is playing an increasingly important role. we look forward to future research findings about 112671-42-8.

Reference:
Patent; Yantai Xianhua Chemical Technology Co., Ltd.; Xing Qifeng; Feng Peichuan; Chen Yue; Hu Lingfeng; Chen Yili; (28 pag.)CN110698458; (2020); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 610-97-9 name is Methyl 2-iodobenzoate, 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. 610-97-9

Example 1Tert-Butoxy-[4-(4-methoxy-3, 5-dimethyl -phenyl)-2-methyl-1-oxo-1,2-dihydro-isoquinolin-3-yl]-acetic acidStep A Preparation of 2-(3-Hydroxy-prop-1-ynyl)-benzoic acid methyl ester:[00131] To a suspension of compound 1 (88.0 g, 335.9 mmol), compound 2 (28.3 g, 503.8 mmol), copper iodide (1 .2 g, 6.7 mmol), Pd(PPh3) CI2 (7.0 g, 10.0 mmol) and Et3N (triethylamine) (68.0 g, 671 .8 mmol) in acetonitrile (1 L) was bubbled N2 for 20 min. The resultant mixture was stirred at reflux under N2 for 3 hr. The reaction mixture was filtered and the filtrate was concentrated to dryness. The residue was purified by chromatography to afford title product. (m=58.8 g, yield=92.0%). 1 HNMR: (400MHz, d6-DMSO) delta 2.48 (t, J=6.2 Hz, 1 H), 3.88 (s, 3 H), 4.52 (d, J=5.6 Hz, 2 H), 7.32 (t, J=7.6Hz, 1 H), 7.41 (t, J=7.6Hz, 1 H), 7.51 (d, J=7.6Hz, 1 H), 7.90 (d, J=7.2Hz, 1 H).

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

Reference:
Patent; GLAXOSMITHKLINE LLC; DE LA ROSA, Martha Alicia; HAYDAR, Simon, N.; JOHNS, Brian Alvin; VELTHUISEN, Emile Johann; WO2012/102985; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

608-28-6, A common heterocyclic compound, 608-28-6, name is 2-Iodo-1,3-dimethylbenzene, molecular formula is C8H9I, 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.

One 250ml flask was charged with 4-phenyl imidazole (7.08g, 49.12mmole), 2- iodo-m-xylene(9.5g, 40.93mmole), copper (5.721g, 90.046mmole); 18-crown-6 (1.08Ig, 4.09 mmole), K2CO3 (21.49g, 155.53 mmole) and tetrahydronaphthalene (90ml). Reaction was heated to 180 C for 68hrs. Reaction mixture was then filtered through Celite and the filtrate was concentrated to dryness. The residue was subjected to kugelrohr distillation and 4g of ligand was obtained.(39%).

The synthetic route of 608-28-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSAL DISPLAY CORPORATION; WO2006/121811; (2006); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

2401-21-0, 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 2401-21-0 as follows.

EXAMPLE 3 1-(4′-Amino-3′-chloro-5′-trifluoromethyl-phenyl)-2-tert.pentylamino-ethanol hydrochloride by method B 0.37 gm of 1-(4′-amino-3′-trifluoromethyl-phenyl)-2-tert.pentylamino-ethanol hydrobromide and 0.2 ml of pyridine were dissolved in 30 ml of tetrahydrofuran, and the solution was cooled to 0¡ã C. 0.3 gm of iodobenzene dichloride was added, the mixture was held for 2 hours at 0¡ã C., and 0.1 gm of iodobenzene dichloride was again added. After standing for 20 hours at about 4¡ã C., the solution was evaporated, distributed between ethyl acetate and water, the aqueous phase was made alkaline with 2N ammonia, and the solution was again extracted with ethyl acetate. The organic phase was washed with water, dried and a few drops of isopropanolic 4N hydrochloric acid were added. The precipitated hydrochloride of the above-mentioned compound was suction-filtered off and washed with ether. M.p. 176¡ã-178¡ã C. (decomp.).

According to the analysis of related databases, 1,2-Dichloro-3-iodobenzene, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Boehringer Ingelheim GmbH; US4119710; (1978); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding some certain compound to certain chemical reactions, such as: 71838-16-9, name is 2-Bromo-1-iodo-4-methylbenzene, 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 71838-16-9. 71838-16-9

General procedure: Et2NH (20 mL), THF (20 mL), 1-bromo-2-iodobenzene (2.2 mL g,18 mmol), and trimethylsilylacetylene (2.9 mL, 21 mmol) weresuccessively added to a flask containing PdCl2(PPh3)2 (0.25 g,0.35 mmol) and CuI (0.067 g, 0.35 mmol). The mixture was stirredat room temperature for 12 h and then evaporated. The residuewasdiluted with hexane/AcOEt (5:1) and washed with 1M aqueousHCl. The organic layer was dried over Na2SO4 and evaporated. Purificationof the residue by silica-gel column (hexane) gave 1-bromo-2-[2-(trimethylsilyl)ethynyl]benzene [38274-16-7] (1a?) asa pale yellow clear liquid (4.12 g, 16.3 mmol, 92% yield).nBuLi (2.65M in hexane, 701 mL, 1.86 mmol) was added to astirred solution of 1a? (472 mg, 1.86 mmol) in THF (4 mL) at 78 C.After 0.5 h, Me2SiCl2 (223 mL, 1.86 mmol) was added to the mixtureat that temperature. Then the mixture was warmed to room temperatureand stirred for 2 h. MeOH (0.5 mL) and Et3N (290 mL,2.08 mmol) were successively added to the reaction mixtureat 78 C. After removing the cooling bath, the resultant mixturewas stirred at room temperature for 1 h. The mixturewas quenchedwith water and extracted with hexane/AcOEt (30:1) three times.The combined organic layer was dried over Na2SO4 and evaporated.The residuewas purified by flash column chromatography (hexane/AcOEt 40:1). The title compound,1-(methoxydimethylsilyl)-2-[2-(trimethylsilyl)ethynyl]benzene (1a), was obtained as a pale yellowliquid (0.721 g, 2.75 mmol, 71% yield). 1H NMR (500 MHz, CDCl3,7.26 ppm) d 0.25 (s, 9H), 0.47 (s, 6H), 3.56 (s, 3H), 7.30e7.34 (m, 2H),7.48e7.50 (m, 1H), 7.59e7.61 (m, 1H); 13C NMR (125 MHz, CDCl3,77.0 ppm) d 1.8, 0.3, 50.9, 96.9, 106.4, 127.7, 127.7, 129.2, 132.8,134.0, 140.8; IR (neat) 3073, 3052, 2959, 2831, 2155, 1429 cm1;HRMS (EI) calcd for C14H22OSi2 [M] 262.1209, found 262.1209.The substrates 1b-l, and 1p were synthesized by the samemanner as described for the preparation of 1a.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2-Bromo-1-iodo-4-methylbenzene.

Reference:
Article; Kinoshita, Hidenori; Fukumoto, Hiroki; Ueda, Akihiro; Miura, Katsukiyo; Tetrahedron; vol. 74; 14; (2018); p. 1632 – 1645;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

5398-69-6, A common heterocyclic compound, 5398-69-6, name is 2-Iodo-3-nitrobenzoic acid, molecular formula is C7H4INO4, 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.

Reference Example 116 methyl 2-iodo-3-nitrobenzoate A mixture of 2-iodo-3-nitrobenzoic acid (31.0 g, 106 mmol) and concentrated sulfuric acid (24.9 mL, 317 mmol) in methanol (600 mL) was heated under reflux for 12 hr. The solvent was evaporated under reduced pressure and the residue was extracted with methylene chloride. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and water, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by recrystallization (chloroform /hexane) to give the title compound (31.0 g, yield 95%). 1H-NMR (DMSO-d6) delta: 3.90 (3H, s), 7.70 (1H, t, J = 7.6 Hz), 7.82 (1H, dd, J = 7.6, 1.2 Hz), 7.98 (1H, dd, J = 7.6, 1.2 Hz).

The synthetic route of 5398-69-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2141150; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 66416-72-6, name is 4-Bromo-2-iodoaniline, molecular formula is C6H5BrIN, 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. 66416-72-6

Step 1 : Preparation of 4-bromo-1-chloro-2-iodobenzeneterf-Butyl nitrite (11.1 ml, 93.3 mmol) is added to a suspension of copper(ll) chloride (10.04 g, 75 mmol) in acetonitrile (224 ml) and the mixture is heated with stirring to 60 0C. A solution of 4- bromo-2-iodoaniline (18.54 g, 62 mmol) in acetonitrile (56 ml) is added dropwise over about an hour, and once the addition is complete the mixture is stirred at 60 0C for 2 hours. The mixture is cooled to room temperature, poured into 20% aqueous hydrochloric acid (1.3 litres) and extracted with diethyl ether (1.5 litres). The organic extract is separated and the aqueous re- extracted with ether (1 litre). The organic extracts are combined and dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated in vacuo. The residue is further purified by column chromatography on silica gel to give 4-bromo-1-chloro-2-iodobenzene (8.62 g) as an oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 66416-72-6, its application will become more common.

Reference:
Patent; SYNGENTA LIMITED; WO2008/145336; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com