Triphenylphosphine → tert-Butyl N-(2-bromoethyl)carbamate

Participants

Reaction Conditions

Reaction Steps

At 0-10° C. and under an atmosphere of nitrogen, a solution of triphenylphosphine (33.7 g, 128.53 mmol, 1.29 equiv.) in dichloromethane (80 mL) was added dropwise to a stirred solution of tert-butyl 2-hydroxyethylcarbamate (20.1 g, 99.75 mmol, 1.00 equiv.) and N-bromosuccinimide (23.6 g, 132.58 mmol, 1.33 equiv.) in dichloromethane (80 mL). The resulting solution was stirred at 10-15° C. for about 16 hours. The reaction mixture was washed with water (2×100 mL), the organic phase was dried over anhydrous sodium sulfate, and then concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether (60:1)) to give the title product as a light-yellow oil (8.5 g; yield=36%). 1H NMR (300 MHz, CDCl3) δ: 4.98 (b, 1H), 3.45-3.55 (m, 4H), 1.41 (s, 9H).

Provenance & Evidence