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

Participants

Reaction Conditions

Reaction Steps

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]+.

Provenance & Evidence