Sodium Hydroxide → 2-(3,4-Dichloro-phenyl)-oxirane

Temperature

0 °C

To a solution of 2-bromo-1-(3,4-dichlorophenyl)ethanone (5.1 g, 18.96 mmol) in methanol (50 mL) at 0° C. was added sodium borohydride (2.1 g, 56.98 mmol). The reaction mixture was stirred at 0° C. for 1 hour. The pH was adjusted to 12 using 2 M sodium hydroxide solution, the solvent was then removed under reduced pressure and the residue was dissolved in dichloromethane. The resultant solution was washed with brine, dried over sodium sulfate, and concentrated under reduced pressure to give 2-(3,4-dichlorophenyl)oxirane (1.79 g, 50% crude). The crude product was used in the next step without further purification: 1H NMR (CDCl3, 500 MHz) 7.41 (d, J=8.5 Hz, 1H), 7.36 (d, J=2.0 Hz, 1H), 7.12 (dd, J=8.5, 2.0 Hz, 1H), 3.81 (dd, J=4.0, 2.5 Hz, 1H), 3.14 (dd, J=5.5, 4.0 Hz, 1H), 2.73 (dd, J=5.5, 2.5 Hz, 1H); ESI MS m/z 189 [M]+.

1. customthe solvent was then removed under reduced pressure
2. dissolutionthe residue was dissolved in dichloromethane
3. washThe resultant solution was washed with brine
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated under reduced pressure

ORD record

ord-e055acaff45a429ebc198503ac47097a

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034899B2