Reaction #5148

Reaction equation

methyl 4-bromomethyl benzoate

triphenylphosphine

→

(4-carbomethoxy)benzyltriphenylphosphonium bromide

Yield 90.9%

Solvents

toluene

Conditions

Workup

1. 1
   OtherTo a 2 L 3-neck round bottom flask fitted with a glass stopper, rubber septum
2. 2
   Temperaturereflux condenser with a nitrogen inlet tube
3. 3
   TemperatureAfter cooling to room temperature
4. 4
   Otherthe reaction vessel was placed in an ice bath
5. 5
   FiltrationThe resulting precipitate was filtered
6. 6
   Washwashed with toluene
7. 7
   Otherdried in a vacuum oven

Procedure

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-bromomethyl benzoate, 81.74 g (311 mmol) triphenylphosphine, and 744 mL toluene. The solution was heated at 80° C. for 5 h. After cooling to room temperature, the 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.: 1H NMR (CDCl3, 200 MHz) d 3.86 (s, 3H), 5.70 (d, J=15.3 HZ, 2H), 7.24 (m, 4H), 7.71 (m, 15H).

Source