反応 #11177

反応方程式

2-chloro-4-nitrotoluene

NBS AIBN

bromide

triphenylphosphine

→

phosphonium

収率 34.0%

(2-Chloro-4-nitrobenzyl)(triphenyl)phosphonium bromide

収率 34.0%

溶媒

benzene

反応条件

後処理

1. 1
   その他the displacement reaction
2. 2
   workup.WAITwas performed at 20° C. for 7 d

実験手順

Bromination of 2-chloro-4-nitrotoluene with NBS/AIBN, followed by reaction of the crude bromide with triphenylphosphine, using the procedure described in example 102, except that the reaction time for the bromination was 24 h and the displacement reaction was performed at 20° C. for 7 d, gave the crude phosphonium salt (559) (34%) as a light brown solid, mp (benzene) 70–75° C. (dec). 1H NMR [(CD3)2SO] δ 8.21 (d, J=2.5 Hz, 1H), 8.13 (dd, J=8.7, 2.5 Hz, 1H), 7.94 (td, J=7.5, 1.6 Hz, 3H), 7.80–7.66 (m, 12H), 7.43 (dd, J=8.5, 2.6 Hz, 1H), 5.33 (d, J=15.7 Hz, 2H). FABMS found M+=432.0916, 434.0904. C25H20ClNO2P requires 432.0921, 434.0891.

出典