Chloroform → [(4-Nitrophenyl)methyl](triphenyl)phosphanium bromide

HRID 1656580Notes

Reaction equation

HRID 1656580 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][Br:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:12]1([P:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(Cl)(Cl)Cl>C1COCC1>[Br-:9].[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][P+:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 11776TriphenylphosphineHCID 660114-Nitrobenzyl bromide

Product 1

HCID 197008[(4-Nitrophenyl)methyl](triphenyl)phosphanium bromideYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-nitrobenzylbromide (25.0 g, 0.116 mol), triphenylphosphine (30.4 g, 0.116 mol) and chloroform (120 ml) was refluxed for 2 hours with stirring. The mixture was cooled to room temperature, diluted with THF (250 ml) and cooled in a freezer for 4 hours. The solid was collected and dried under vacuum to give p-nitrobenzyl triphenylphosphonium bromide (54.8 g, 99%).

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperaturecooled in a freezer for 4 hours
  3. customThe solid was collected
  4. customdried under vacuum

Sources & evidence

ORD record
ord-583a7aa1732a406496c715997d91d913
Source dataset
uspto-grants-1993_10
Patent number
US05254655

Reaction notes

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