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