Reaktion #11175

Reaktionsgleichung

2-chloro-3-nitrotoluene

NBS AIBN

bromide

triphenylphosphine

→

phosphonium

Ausbeute 44.0%

(2-Chloro-3-nitrobenzyl)(triphenyl)phosphonium bromide

Ausbeute 44.0%

Lösungsmittel

CH2Cl2 benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe displacement reaction
2. 2
   workup.WAITwas performed at 70° C. for 1 d

Vorschrift

Bromination of 2-chloro-3-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 2 h and the displacement reaction was performed at 70° C. for 1 d, gave the phosphonium salt (554) (44%) as a light brown solid, mp (CH2Cl2/benzene) 224–228° C. 1H NMR (CDCl3) δ 8.09 (br d, J=8.3 Hz, 1H), 7.86–7.63 (m, 16H), 7.34 (t, J=8.1 Hz, 1H), 5.95 (d, J=14.6 Hz, 2H). Found: C, 58.68; H, 4.12; N, 2.79. C25H20BrclNO2P requires C, 58.56; H, 3.93; N, 2.73.

Quelle