Pyridine → 2-Bromoethyl-3-chlorobenzoate

Participants

Reaction Steps

To a solution of 3-chlorobenzoyl chloride (2) (0.21 g, 2.8 mmol) and pyridine (0.46 mL, 5.7 mmol) in anhydrous dichloromethane (10 mL) at room temperature was (dropwise) added 2-bromoethanol (1) (0.23 mL, 3.1 mmol). The reaction mixture was stirred for 2 h at room temperature and quenched with 1N HCl. The organic phase was washed with saturated aqueous solution of NaHCO3, brine and then dried over anhydrous MgSO4. The crude product was purified by silica gel chromatography to give 2-bromoethyl 3-chlorobenzoate (3) as colorless oil (0.64 g). 1H NMR (CDCl3): δ 8.04 (t, J=1.8 Hz, 1H), 7.98-7.93 (m, 1H), 7.58-7.52 (m, 1H), 7.40 (t, J=8.4 Hz, 1H), 4.63 (t, J=6.0 Hz, 2H), 3.64 (t, J=6.0 Hz, 2H)

Provenance & Evidence