Propylene Oxide → 1-(2-Bromo-6-chlorophenyl)propan-2-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of LDA (6 mL, 12 mmol) in THF (10 mL) was added 3-chlorobromobenzene (1.91 g, 10.0 mmol) in THF (5 mL) at −78° C. under nitrogen, the resulting mixture was stirred at −78° C. for 1 h, then a solution of propylene oxide (1.7 g, 30 mmol) in THF (5 mL) was added. The mixture was slowly warmed to rt. The mixture was quenched with sat. aq NH4Cl (10 mL), then extracted with EtOAc (50 mL). The organic phase was washed with brine (10 mL) and dried over anhydrous sodium sulfate. The crude material was purified by silica gel chromatography Hexane/EtOAc (80:20) to give the title compound as a yellow oil. 1H NMR (CDCl3, 400 MHz): δ=1.34 (d, J=6.1 Hz, 3H), 1.49 (d, J=5.8 Hz, 1H), 3.11-3.26 (m, 2H), 4.20-4.31 (m, 1H), 7.03 (t, J=8.0 Hz, 1H), 7.36 (dd, J=8.0, 1.1 Hz, 1H), 7.50 (dd, J=8.0, 1.1 Hz, 1H).

Provenance & Evidence