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

Temperature

12.5 °C

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).

1. washThe reaction mixture was washed with water (2×100 mL)
2. dry with materialthe organic phase was dried over anhydrous sodium sulfate
3. concentrationconcentrated in vacuo
4. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether (60:1))

ORD record

ord-cbab61d47d8a4f32bf7140feb48f1952

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778998B2