Benzyl chloroformate → 914452-60-1

Participants

Reaction Steps

In a 500 mL flask, (4-bromophenyl)methanaminium chloride (10.0 g, 44.9 mmol) and sodium hydroxide (4.00 g, 100 mmol) were dissolved in tetrahydrofuran (80 mL) and water (80 mL). The flask was placed in an ice water bath and benzyl carbonochloridate (7.06 mL, 49.4 mmol) was added dropwise. The reaction was allowed to stir for 3 h. The reaction was then poured into brine solution and extracted with ethyl acetate (3×150 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated to give the title compound as a white solid (14.1 g, 97%): 1H NMR (400 MHz, DMSO-d6) δ 7.88 (t, J=6.1 Hz, 1H), 7.58-7.46 (m, 2H), 7.46-7.27 (m, 5H), 7.23 (d, J=8.2 Hz, 2H), 5.06 (s, 2H), 4.19 (d, J=6.2 Hz, 2H); 13C NMR (101 MHz, DMSO-d6) δ 156.34, 139.19, 137.05, 131.10, 129.22, 128.32, 127.78, 127.73, 119.79, 65.44, 43.22; ESIMS m/z 320 ([M+H]+).

Provenance & Evidence