Chloroform → 3-Bromo-2-(4-methoxyphenyl)benzo[b]thiophene

Participants

Reaction Steps

A mixture of the dibromobenzothiophene (11 g, 37.7 mmol), p-methoxyphenylboronic acid (5.7 g, 37.7 mmol), Pd(OAc) to (58 mg, 0.26 mmol) and tri-ortho-tolyl phosphine (237 mg) in 38 mL THF was treated with 38 mL 2 M Na2CO3 and refluxed in the absence of light overnight. Diluted with 100 mL EtOAc and separated the layers. The aqueous layer was extracted with EtOAc (50 mL). The combined organic layer was dried over MgSO4 and concentrated to an oil which was purified by chromatography (SiO2 ; stepwise 5 then 8% CHCl3 in hexanes) to recover 9.34 g (29.3 mmol, 78%) of the desired compound as a white solid.

Provenance & Evidence