Diiodomethane → 2-(4-Bromophenyl)-2-methyloxirane

Participants

Reaction Conditions

Reaction Steps

2-(4-Bromo-phenyl)-2-methyl-oxirane was synthesized according to the scheme shown in FIG. 5. 4′-Bromoacetophenone (0.60 g, 3 mmol) and diiodomethane (1.6 g, 6 mmol) were dissolved in 12 mL dry THF. Methyllithium (5.6 mL, 1.6M in ether) was added via syringe in 10 min at 0° C. The resulting clear yellow solution was stirred at 0° C. for 30 min and was then warmed up to room temperature. After stirring at room temperature for 1 hour, the reaction mixture was quenched with ice. The resulting mixture was extracted with EtOAc, washed with brine and dried over Na2SO4. After removing the solvent, fairly pure product (0.62 g) was obtained as yellow solid, which was directly used for next step without further purification. ESI MS m/z 213, 215 (M+H).

Provenance & Evidence