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

Participants

Reaction Steps

A mixture of 46 g (0.2 mole) of methyl-α-bromotoluate and 105 g (0.4 mole) of triphenyl phosphine in 800 ml of dry benzene was refluxed for two hours. After 15 minutes, the phosphonium bromide started precipitating out from the solution. After cooling the flask to room temperature, the solid was filtered, washed with plenty of petroleum ether and dried. The yield was 98 g m.p. 258°-260° C. The infrared spectrum showed absorption at 1720 cm-1 ##STR10## NMR (CDCl3) showed 3.8 ##STR11## 5.5-5.8 (d, --CH2 -p+, 2), and 7-8 (m,aromatic, 19). The phosphonium bromide was used in the next stop without further purification.

Provenance & Evidence