4-Bromobenzoyl chloride → Tert-butyl 4-bromobenzoate

Participants

Reaction Steps

To a solution of 4-bromobenzoyl chloride (25.08 g, 114 mmol) in THF (120 mL) at ±78° C. was added potassium tert-butoxide (120 mL, 1 M in THF, 120 mmol). The reaction mixture was warmed from −78° C. to room temperature over 2 h, and diluted with diethyl ether. The organic phase was washed with saturated NaHCO3 (2×), brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (5% ethyl acetate in hexanes) gave tert-butyl 4-bromobenzoate (27.96 g, 95%) as a colorless oil: 1H NMR (600 MHz, CDCl3) δ 7.84 (d, J=8.5 Hz, 2H), 7.54 (d, J=8.5 Hz, 2H), 1.59 (s, 9H); ESIMS calcd 257.0 (M++H), found 257.1 (M++H).

Provenance & Evidence