Bromoform → 1,8,8-Tribromo-bicyclo[5.1.0]octane

Participants

Reaction Steps

To a solution of 12 g (6.86 mmol) of 1-bromo-cycloheptene in 52 g (206 mmol) of bromoform and 56 g of methylene chloride was added 0.73 g (1.59 mmol) of N,N′-dibenzyl-N,N,N′,N′-tetramethylethylenediammonium dibromide and 18.8 g (152 mmol) of 45% aqueous potassium hydroxide. After 24 hours the reaction mixture was poured onto water. The resulting mixture was transferred to a separatory funnel and the phases were separated. To the isolated organic layer was added 0.73 g (1.59 mmol) of N,N′-dibenzyl-N,N,N′,N′-tetramethylethylenediammonium dibromide and 18.8 g (152 mmol) 45% aqueous potassium hydroxide. After 24 hours the reaction mixture was poured onto water. The resulting mixture was transferred to a separatory funnel and the phases were separated. The isolated organic layer was dried over magnesium sulfate and filtered. The filtrate was dried in vacuo. The residue obtained was purified by column chromatography with hexanes. The resulting oil was purified by vacuum distillation to yield 7.8 g of 1,8,8-tribromo-bicyclo[5.1.0]octane.

Provenance & Evidence