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

HRID 83990Notes

Reaction equation

HRID 83990 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 dried under vacuum to afford the title compound (8 g). Mass (m/z): 433.9 (M++1)

Workup

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

Sources & evidence

ORD record
ord-56aed7c4d9224c85a8776f9b4aae7f19
Source dataset
uspto-grants-2014_09
Patent number
US08846910B2

Reaction notes

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