Bromide ion → (2-Chloro-4-nitrobenzyl)(triphenyl)phosphonium bromide

HRID 11081

Reaction equation

HRID 11081 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH3:11].C1C(=O)N([Br:19])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.[Br-].[C:33]1([P:39]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>C1C=CC=CC=1>[Br-:19].[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][P+:39]([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 259Bromide ionHCID 84912-Chloro-4-nitrotolueneHCID 11776TriphenylphosphineHCID 86630000Nbs aibn

Product 1

HCID 87898987(2-Chloro-4-nitrobenzyl)(triphenyl)phosphonium bromideYield 34%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

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.

Workup

  1. customthe displacement reaction
  2. waitwas performed at 20° C. for 7 d

Sources & evidence

ORD record
ord-b77c515b4e7647afacc2b1635151178a
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Linked notes

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