Methanesulfonyl chloride → 2-(2-bromophenyl)-3-methyl-2H-azirine

Participants

Reaction Steps

To a solution of 1-(2-bromophenyl)propan-2-one oxime (1.36 g, 5.96 mmol) and TEA (722 mg, 7.15 mmol) in anhydrous THF (50 mL) at RT was added dropwise a solution of methanesulfonyl chloride (819 mg, 7.15 mmol) in anhydrous THF (5 mL). After stirring at RT for 1 h, 1,8-diazabicyclo[5.4.0]undec-7-ene (2.26 g, 14.9 mmol) was added and stirring continued at RT for 1 h. The reaction mixture was passed through a pad of SiO2, concentrated in vacuo, and purified by SiO2 chromatography eluting with petroleum ether/EtOAc (10:1) to afford 2-(2-bromophenyl)-3-methyl-2H-azirine as yellow oil (758 mg, yield, 60.5%). MS (ESI): m/z=242.1 [M+33]+.

Provenance & Evidence