Triphenylphosphine → [4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromide

Participants

Reaction Conditions

Reaction Steps

To a 2 L 3-neck round bottom flask fitted with a glass stopper, rubber septum, and reflux condenser with a nitrogen inlet tube, was added 64.90 g (283 mmol) methyl 4-bromomethylbenzoate, 81.74 g (311 mmol) triphenylphosphine, and 744 mL toluene. The solution was heated at 80° C. for 5h. After cooling to room temperature, reaction vessel was placed in an ice bath. The resulting precipitate was filtered, washed with toluene, and dried in a vacuum oven to afford 126.35 g (89% (4-carbomethoxy) benzyltriphenylphosphonium bromide) as a white solid, mp.=248°-250° C. (reported in V. Sankaran and C. S. Marvel, J. Polym. Sci, Poly. Chem. Ed , 17, 3949 (1979) as 258°-260° C.): 1H NMR (CDCl3, 200 MHz) δ 3.86 (s,3H), 5.70 (d,J=15.3 Hz, 2H), 7.24 (m,4H), 7.71 (m, 15 H).

Provenance & Evidence