Benzyl chloroformate → Benzyl (3-bromophenyl)carbamate

Participants

Reaction Steps

To a mixture of 3-bromoaniline (0.500 g), 2 mol/L aqueous sodium hydroxide (2.18 mL) and tetrahydrofuran (3.63 mL) was added dropwise benzyl chloroformate (0.498 mL), and the resulting mixture was stirred at room temperature for 3.5 hours. The reaction mixture was partitioned between ethyl acetate (35 mL) and water (10 mL). The organic layer was washed with brine (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=8/1) to give the title compound (0.897 g).

Provenance & Evidence