1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (S)-1-Phenylethyl 2-bromo-2-phenylacetate

Participants

Reaction Steps

To a mixture of α-bromophenylacetic acid (11.20 g, 52.1 mmol), (S)-(−)-1-phenylethanol (8.2 mL, 67.9 mmol) and DMAP (0.63 g, 5.2 mmol) in CH2Cl2 (100 mL). was added EDAC (13.80 g, 72.0 mmol). The resulting mixture was stirred at room temperature for 3 hours then diluted with ethyl acetate (200 mL), washed with water (2×100 mL) and brine (100 mL). The organic layer was dried (MgSO4), filtered, and concentrated then purified by column chromatography to provide the title compound (12.6 g, 76% yield).

Provenance & Evidence