Methylenecycloheptane → Bromomethanesulfonylmethylene cycloheptane

Participants

Reaction Steps

A mixture of methylenecycloheptane (3.3 g) and bromomethanesulfonyl bromide (7.14 g) in methylene chloride (10 mL) was irradiated at -20° C. with an ultraviolet lamp for 1 hour. Evaporation of the solvent gave a solid which was washed with pentane. This solid (9.7 g) was dissolved in methylene chloride (150 mL), chilled in ice and treated dropwise with a solution of triethylamine (3.3 g) in methylene chloride (20 mL). The reaction mixture was stirred for 0.5 hours, washed with dilute HCl and water. The organic layer was separated, dried over anhydrous magnesium sulfate and the methylene chloride removed in vacuo to give oily bromomethanesulfonylmethylene cycloheptane (7.0 g, 96% yield) which was characterized by IR and NMR spectroscopy.

Provenance & Evidence