1-Bromo-3-chlorobenzene → HCID 66763576, compound

Participants

Reaction Conditions

Reaction Steps

To 1-bromo-3-chlorobenzene (480 mg, 2.51 mmol) in diethyl ether (10 mL), at −78° C., was added t-butyllithium (3.0 mL of a 1.7 M solution in hexanes, 5.0 mmol) dropwise. After 1 h, a solution of 1-(3-methoxybenzyl)piperidin-4-one (500 mg, 2.28 mmol) in diethyl ether (5 mL) was added dropwise. The reaction mixture was stirred at −78° C. for 0.5 h, warmed to ambient temperature and quenched with saturated ammonium chloride. The organic layer was separated, washed with brine, dried over sodium sulfate and concentrated in vacuo. Purification by silica gel chromatography (10% ethyl acetate/methylene chloride to ethyl acetate) gave 4-(3-chlorophenyl)-1-(3-methoxybenzyl)piperidin-4-ol (668 mg, 80%) as an oil: 1H NMR (CDCl3, 300 MHz) δ 7.53-7.52 (m, 1H), 7.40-7.36 (m, 1H), 7.30-7.20 (m, 3H), 6.96-6.93 (m, 2H), 6.82-6.79 (m, 1H), 3.82 (s, 3H), 3.58 (s, 2H), 2.82-2.70 (m, 2H), 2.49-2.41 (m, 2H), 2.18-2.08 (m, 2H), 1.73-1.67 (m, 2H), 1.60 (s, 1H).

Provenance & Evidence