Sodium borohydride → HCID 86671392, compound

Participants

Reaction Steps

To a stirred suspension of the mixture of 2-bromo-1-(3-methyl-4-nitrophenyl)ethanone and 2-chloro-1-(3-methyl-4-nitrophenyl)ethanone (6.23 g) in ethanol (100 ml) at 5° C. was added portionwise over 5 min NaBH4 (913 mg). The reaction mixture was then stirred at room temperature for 1 hour to afford a dark yellow solution. TLC analysis showed the reaction was complete. Sodium methoxide (652 mg) was then added and the reaction mixture was stirred at room temperature overnight. TLC analysis showed a small amount of starting material remaining and so the reaction mixture was stirred at 40° C. for 1 h. The reaction mixture was then poured into EtOAc and extracted with saturated brine. The organic layer was dried over Na2SO4 and concentrated in vacuo to afford (RS)-2-(3-methyl-4-nitrophenyl)oxirane (4.63 g, 94% over 2 steps) as a yellow oil. MS (EI): 179 (M+), 164 ([M-CH3]+), 162 [M-OH]+), 132 [M-OH—NO]+), 103, 77.

Provenance & Evidence