Bromoform → 3-(1,2,2-Tribromo-cyclopropyl)-propionic acid ethyl ester

Participants

Reaction Steps

To a solution made of 12.12 g (58 mmol) of 4-bromo-pent4-enoic acid ethyl ester and 51 g (202 mmol) of bromoform and 100 g of methylene chloride was added 2.0 g of N,N′-dibenzyl-N,N,N′,N′-tetramethylethylenediammonium dibromide and 27.1 g (218 mmol) of 45% aqueous potassium hydroxide. The reaction mixture was stirred rapidly for 4 days. The resulting mixture was transferred to a separatory funnel and the phases were separated. The solvent was removed from the isolated organic layer in vacuo. This residue was extracted with hexanes from water. The resulting mixture was transferred to a separatory funnel and the phases were separated. The organic layer was dried over MgSO4 and filtered. The solvent was removed from the filtrate in vacuo. This residue was purified by column chromatography with 10% diethyl ether/hexanes to yield 14.6 g (66.3% of theory) of 3-(1,2,2-tribromo-cyclopropyl)-propionic acid ethyl ester.

Provenance & Evidence