Triphenylphosphine → (3-(Ethoxycarbonyl)propyl)triphenylphosphonium Bromide

Participants

Reaction Conditions

Reaction Steps

A mixture of triphenylphosphine (24.6 g; 0.0936 mol) and ethyl 4-bromobutyrate (from Aldrich) (14.4 mL; 0.101 mol) was heated from room temperature to 105° C. over a period of 15-20 minutes; then heating was continued at 105° C. for 10 minutes. The solution was allowed to cool, but while still warm, diethyl ether (50 mL) was cautiously added via a condenser. The resultant gum was triturated to obtain a white powder. Ether was decanted, fresh diethyl ether (50 mL) was added, and trituration continued for 10 min. The reaction mixture was filtered, the filter cake washed with diethyl ether, and then solvent was removed under vacuum from the combined filtrate and washings to obtain a mixture of oil and solids. This mixture was heated to 100° C.; was cautiously treated with diethyl ether (2×55 mL); and the trituration, filtration, and concentration sequence described above was repeated. The two batches of white solids obtained from this process were combined, triturated with toluene (150 mL), filtered, and the collected solids were washed with toluene and dried under high vacuum to obtain the title salt (53). FABMS 377 (M+) mp 177-179° C.

Provenance & Evidence