Borane;tetrahydrofuran → 2-(4-Hydroxymethyl-phenylsulfanylmethyl)-benzoic acid 2,2,2-trichloro-ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(4-Carboxy-phenylsulfanylmethyl)-benzoic acid 2,2,2-trichloro-ethyl ester (80 mg, 0.191 mmol) in THF (1 mL) at 0° C. was added dropwise BH3-THF (0.4 mL, 1.0M solution in THF). The reaction was stirred at 0° C. for 0.5 h after the addition was complete, thereafter the cooling bath was removed and the reaction was stirred for 2 h at rt. The reaction was quenched at 0° C. by careful addition of THF/H2O, 80/20 followed by dropwise addition of 2M HCl. The mixture was stirred for an additional 10 minutes and thereafter diluted with water. THF was removed and the water phase was extracted with DCM and the combined organic phase was dried through a phase separator and concentrated to give the titled compound (70 mg, 91%) as an oil; 1H NMR (400 MHz, CDCl3): δ 4.53 (s, 2H), 4.64 (s, 2H), 4.94 (s, 2H), 7.19-7.30 (m, 5H), 7.30-7.36 (m, 1H), 7.37-7.44 (m, 1H), 8.06 (d, 1H).

Provenance & Evidence