Triphenylphosphine → [(4-Bromophenyl)methyl]triphenylphosphanium bromide

HRID 1892146Notes

Reaction equation

HRID 1892146 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Br)=[CH:4][CH:3]=1.[C:10]1([P:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1(C)C(C)=CC=CC=1>[Br-:1].[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][P+:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 685274-Bromobenzyl bromide

Product 1

HCID 2724858[(4-Bromophenyl)methyl]triphenylphosphanium bromideYield 156.1%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 1-bromo-4-(bromomethyl)benzene (5 g) and triphenylphosphine (5.24 g) in xylene (20 mL) were heated to reflux for 18 hours. The reaction mixture was cooled, filtered, washed with hexane and tried under vacuum to afford the title compound (8 g).

Workup

  1. temperaturewere heated
  2. temperatureto reflux for 18 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. washwashed with hexane

Sources & evidence

ORD record
ord-7ab6c568cd874e9ba839136bde57e976
Source dataset
uspto-grants-2013_08
Patent number
US08507670B2

Reaction notes

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