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

Temperature

-78 °C

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).

1. temperatureThe mixture was slowly warmed to rt
2. customThe mixture was quenched with sat. aq NH4Cl (10 mL)
3. extractionextracted with EtOAc (50 mL)
4. washThe organic phase was washed with brine (10 mL)
5. dry with materialdried over anhydrous sodium sulfate
6. customThe crude material was purified by silica gel chromatography Hexane/EtOAc (80:20)

ORD record

ord-0fc21f2aa7aa4a20ad35b04e22efd8e2

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08022206B2