Chemical Properties
WHITE CRYSTALLINE POWDER
Uses
(Ethoxycarbonylmethyl)triphenylphosphonium bromide, is used as a pharmaceutical intermediate.
reaction suitability
reaction type: C-C Bond Formation
Synthesis
Ethoxycarbonylmethyltriphenylphosphonium bromide was prepared as follows: ethyl acetate (5.0 L) was added to triphenylphosphonium, and ethyl bromoacetate (665 g, 4.01 mol) was added dropwise to the mixture with stirring, and after the dropwise addition the reaction mixture was stirred at room temperature for 24 hours. The mixture was then diafiltered and the filter cake was washed three times with ethyl acetate, using 500 mL each time. Vacuum drying of the filter cake gave ethoxymethyltriphenylphosphonium bromide [Ph 3 PCH 2 CO 2 Et]+Br- (1500 g) as a white solid in 92% yield.
Purification Methods
Wash it with pet ether (b 40-50o) and recrystallise it from CHCl3/Et2O and dry it in a high vacuum at 65o. [Isler et al. Helv Chim Acta 40 1242 1957, Wittig & Haag Chem Ber 88 1654, 1664 1955.]
