Triphenylphosphine → [(3-Carboxy-4-nitrophenyl)methyl](triphenyl)phosphanium bromide

HRID 980464Notes

Reaction equation

HRID 980464 reaction equation
[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]([N+:12]([O-:14])=[O:13])=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7].[C:15]1([P:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1>[Br-:1].[C:28]1([P+:21]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:2][C:3]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:5]([C:6]([OH:8])=[O:7])[CH:4]=2)[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 202215115-(Bromomethyl)-2-nitrobenzoic acid

Product 1

HCID 20221492[(3-Carboxy-4-nitrophenyl)methyl](triphenyl)phosphanium bromideYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 15 g (57.7 millimoles) of 3-bromomethyl-6-nitro-benzoic acid, 15.17 g (57.7 millimoles) of triphenyl phosphine and 70 ml anhydrous toluene is refluxed for 2 hours. The precipitated product is filtered off, washed with ether and dried. Thus 21.15 g of the title compound are obtained, yield 71%.

Workup

  1. temperatureis refluxed for 2 hours
  2. filtrationThe precipitated product is filtered off
  3. washwashed with ether
  4. customdried

Sources & evidence

ORD record
ord-f5ed7dd7722c4f5ca5fad7df2ab157c0
Source dataset
uspto-grants-1987_01
Patent number
US04638002

Reaction notes

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