Trifluoroacetic acid → 2-Benzyl-1-benzothiophene

Participants

Reaction Steps

Trifluoroacetic acid (105 mL) was added dropwise over a 35 minute period to a stirred suspension of benzo[b]thiophene-2-yl-(phenyl)-methanol (17.6 g, 73.2 mmol), sodium borohydride (13.75 g, 364 mmol) and ether (1.3 L). After an additional 5 hours the reaction mixture was added to 10% aqueous sodium hydroxide (1.3 L) and stirred for 30 minutes. The layers were separated and the ether phase was washed with brine (500 mL) and dried (MgSO4). The ether phase was concentrated to provide the title compound as a white solid (15.2 g, 92%): NMR (CDCl3); δ 7.73 (d, J=6 Hz, 1H, thiopheneH), 7.65 (d, J=7 Hz, 1H, thiopheneH), 7.20-7.38 (m, 7H), 7.00 (s, 1H, thiopheneH), 4.22 (s, 2H, CH2).

Provenance & Evidence