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 Chemical Company, Milwaukee, Wis.) (14.4 mL; 0.101 mol) was heated from room temperature to 105° C. over a period of 15-20 minutes, and continued heating the resultant solution at 105° C. for 10 minutes. Allowed the solution to cool, but while still warm cautiously added diethyl ether (50 mL) via a condenser. Triturated the resultant gum to obtain a white powder. Decanted, added fresh diethyl ether (50 mL), and continued trituration for 10 min. Filtered the reaction mixture; washed the filter cake with diethyl ether; and under vacuum removed solvent from the combined filtrate and washings to obtain a mixture of oil and solids. Heated this mixture to 100° C.; cautiously treated with diethyl ether (2×55 mL); and repeated the trituration, filtration, and concentration sequence described above. Combined the two batches of white solids obtained from this process, triturated with toluene (150 mL), filtered, washed the collected solids with toluene and dried under high vacuum to obtain the title salt (11). FABMS 377 (M+) mp 177-179° C.

Provenance & Evidence