Chloroiodomethane → 2-(Chloromethyl)-2-(2,4-difluorophenyl)oxirane

Participants

Reaction Steps

To a stirred and cooled (−78° C.) mixture of 2-chloro-1(2,4-difluorophenyl)-1-ethanone (30 g), chloroiodomethane (56.4 g) and tetrahydrofuran 267 ml) was added dropwise a 6% solution of methyllithium-lithiumbromide complex in diethylether (215 ml). The reaction mixture was slowly warmed to room temperature and was then hydrolysed with NH4Cl. Aqueous NaOH was added and the mixture was stirred for 1 hour. The organic layer was separated, washed, dried, filtered and the solvent evaporated. The residue was purified over silica gel (eluent: hexane/CH3COOC2H5 98/2). The solvent of the desired fraction was evaporated, yielding 11 g (16.8%) of 2-(chloromethyl)-2-(2,4-difluorophenyl)oxirane (interm. 1).

Provenance & Evidence