tert-Butanol → tert-Butyl 2-bromobenzoate

Participants

Reaction Steps

To a solution of 2-bromobenzoyl chloride 2.0 g, 9.11 mmol) in dry diethyl ether (40 mL) was added 2-methyl-2-propanol (0.96 mL, 10.02 mmol) followed by 4-(dimethylamino)pyridine (111 mg, 0.911 mmol) and the reaction mixture stirred at room temperature under nitrogen for 48 hours. The resulting white suspension was then partitioned between ethyl acetate (100 mL) and 1 M hydrochloric acid (100 mL). The organic phase was separated, washed with 1 M hydrochloric acid (100 mL), 2 M sodium hydroxide (2×100 mL), water (100 mL) and brine (100 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to give a yellow oil. Purification by flash chromatography using ethyl acetate/hexane as eluant gave the title compound (1.22 g, 52%) as a colorless oil.

Provenance & Evidence