Category: 351005-12-4

351005-12-4, 5-Bromo-1,3-dihydrobenzo[c]thiophene 2,2-dioxide is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

351005-12-4, Dissolve 4-bromo-1, 2-bis-bromomethyl-benzene (J. Org. Chef., 1418-1421, 1985; 3.42 g, 9.96 mmol) in a 2 to 1 mixture of ethanol (EtOH) and THF (1196 mL) and heat the solution to 70C with stirring. Add a solution of Na2S. 9H2O (2.63 g, 10.96 mmol) in water (40 mL), dropwise, over 10 hours using a syringe pump. Continue to heat and stir for another 10 hours. Cool to room temperature and remove the organic solvent under reduced pressure. Add water (200 mL) to the residue and extract the aqueous layer with EtOAc (3 x 200 mL). Combine the organic layers and dry with Na2S04, filter, concentrate and purify by flash column chromatography (silica gel, hexanes) to give 1.27 g of 5-bromo-1, 3-dihydro-benzo [c] thiophene (59%). Dissolve 5-bromo-1, 3-dihydro-benzo [c] thiophene (1. 25 g, 5.79 mmol) in methanol (25 mL) and add oxone (10.7 g, 17. 4 mmol). Stir the reaction mixture for 2 hours at 0C and then add a 1M aqueous sodium bisulfite solution (100 mL). Stir the reaction mixture for 10 minutes and add saturated NaHCO3 solution (200 mL). Extract the aqueous layer with CH2C12 (3 x 100 mL). Combine the organic layers and dry with Na2S04, filter, concentrate and purify by flash column chromatography (silica gel, 0-5% MeOH/CH2Cl2) to give 930 mg of 5-bromo-1, 3-dihydro-benzo [c] thiophene 2, 2-dioxide (65%). Dissolve 5-bromo-1, 3-dihydro-benzo [c] thiophene (860 mg, 3.50 mmol) and hexamethylditin (3 eq. ) in toluene and add tetrakis (tripheuylphosphine) palladium (0) (Pd (PPh3) 4, 0.1 eq. ). Flush the flask with N2 and then heat the mixture to 120C with stirring. Continue to heat the mixture for 5 hours and then cool to room temperature. Add water (50 mL) and extract aqueous layer with EtOAc (3 x 50 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash chromatography (silica gel, 10-30% EtOAc/hexane) to give 1.22 g of the title compound (100%).

The synthetic route of 351005-12-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ELI LILLY AND COMPANY; WO2004/9086; (2004); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

351005-12-4, 5-Bromo-1,3-dihydrobenzo[c]thiophene 2,2-dioxide is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

16. Preparation of 2-(2 ,2-dioxo-2,3-dihydro-1 H-benzo[c]thiophen-5-yl)-4,4,5,5- tetramethyl-[1 ,3,2]dioxaborolane In a screw-capped vessel 5-bromo-1 3-dihydro-benzo[c]thiophene2,2-dioxide (100 mg, 0.40 mmol), bis(pinacolato)diboron (206 mg,0.81 mmol), potassium acetate (119 mg, 1.21 mmol) and Pd(dppf)C12.CH2CI2 (33.1 mg, 0.04 mmol) were suspended in THE SeccoSolv (5 mL).Nitrogen was bubbled through the mixture for 5mm. The reaction mixture was stirred at70C for 15 h. The mixture was diluted with THF (7 mL), filtered and the filtrate wasevaporated to dryness. The crude residue was purified by flash chromatography(heptane/DCM) to yield in 89.0 mg (75 %) of the title compound as an off-white solid.LC/MS (Method B): Rt = 2.53 mm, (M+Na) 317., 351005-12-4

As the paragraph descriping shows that 351005-12-4 is playing an increasingly important role.

Reference£º
Patent; MERCK PATENT GMBH; CANCER RESEARCH TECHNOLOGY LIMITED; SCHIEMANN, Kai; STIEBER, Frank; CALDERINI, Michel; BLAGG, Julian; MALLINGER, Aurelie; WAALBOER, Dennis; RINK, Christian; CRUMPLER, Simon Ross; (127 pag.)WO2015/144290; (2015); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

351005-12-4, 5-Bromo-1,3-dihydrobenzo[c]thiophene 2,2-dioxide is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

16. Preparation of 2-(2 ,2-dioxo-2,3-dihydro-1 H-benzo[c]thiophen-5-yl)-4,4,5,5- tetramethyl-[1 ,3,2]dioxaborolane In a screw-capped vessel 5-bromo-1 3-dihydro-benzo[c]thiophene2,2-dioxide (100 mg, 0.40 mmol), bis(pinacolato)diboron (206 mg,0.81 mmol), potassium acetate (119 mg, 1.21 mmol) and Pd(dppf)C12.CH2CI2 (33.1 mg, 0.04 mmol) were suspended in THE SeccoSolv (5 mL).Nitrogen was bubbled through the mixture for 5mm. The reaction mixture was stirred at70C for 15 h. The mixture was diluted with THF (7 mL), filtered and the filtrate wasevaporated to dryness. The crude residue was purified by flash chromatography(heptane/DCM) to yield in 89.0 mg (75 %) of the title compound as an off-white solid.LC/MS (Method B): Rt = 2.53 mm, (M+Na) 317., 351005-12-4

As the paragraph descriping shows that 351005-12-4 is playing an increasingly important role.

Reference£º
Patent; MERCK PATENT GMBH; CANCER RESEARCH TECHNOLOGY LIMITED; SCHIEMANN, Kai; STIEBER, Frank; CALDERINI, Michel; BLAGG, Julian; MALLINGER, Aurelie; WAALBOER, Dennis; RINK, Christian; CRUMPLER, Simon Ross; (127 pag.)WO2015/144290; (2015); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.351005-12-4,5-Bromo-1,3-dihydrobenzo[c]thiophene 2,2-dioxide,as a common compound, the synthetic route is as follows.

5-Bromo-1 ,3-dihydro-benzo(c)thiophene 2,2-dioxide (500 mg, 2.02 mmol), the previously synthesized tert-butyl 2-(bromozincio)acetate (7.60 m L, 6.07 mmol) and dry THF (5 mL) were placed in flask, the mixture was degassed by nitrogen bubbling for 5 mm. Then Pd2(dba)3 (185 mg, 0.20 mmol) and XPhos (193 mg, 0.41 mmol) were incorporated and the reaction mixture was stirred at 75C for 1 h. The mixture was cooled to rt, EtOAc and water was added and the two-phase mixture was filtered through a pad of Celite. The phaseswere separated, the organic layer was dried over Mg504, filtered and the solution was concentrated to dryness. The crude material was purified by column chromatography eluting with a gradient of Cyclohexane/EtOAc from [100:0] to [70:30]. The product fractions were combined and concentrated to dryness. The residue was triturated with Cyclohexane/Et20 [1:1], filtered and dried under vacuum at 40C. The product tert-butyl 2-(2,2-dioxo-1 ,3-dihydro-2- benzothiophen-5-yl)acetate Ex.46a (421 mg, 74%) was isolated as a white fluffy solid. 1 H NMR (300 MHz, DMSO-d6, d in ppm): 1 .39 (s, 9H), 3.58 (s, 2H), 4.46 (s, 2H), 4.48 (s, 2H), 7.22-7.25 (m, 2H), 7.32 (d, 1 H, J=7.5Hz).

351005-12-4, The synthetic route of 351005-12-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GENFIT; DELHOMEL, Jean-Francois; PERSPICACE, Enrico; MAJD, Zouher; PARROCHE, Peggy; WALCZAK, Robert; (284 pag.)WO2018/138362; (2018); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.351005-12-4,5-Bromo-1,3-dihydrobenzo[c]thiophene 2,2-dioxide,as a common compound, the synthetic route is as follows.

Under classical Heck reaction conditions, 5-Bromo-l,3-dihydro-benzo(c)thiophene 2,2 -dioxide was transformed with PPh3, Pd(OAc)2, TEA, and vinyltrimethylsilane at 90 C in DMF. The crude product was extracted with CH2Cl2 and concentrated. Deprotection in CH2C12/TFA gave the pure product after purification with flash chromatography (CH2Cl2) in high yields.

351005-12-4, As the paragraph descriping shows that 351005-12-4 is playing an increasingly important role.

Reference£º
Patent; VANDERBILT UNIVERSITY; WO2008/24435; (2008); A2;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem