Triphenylphosphine → 2-Chlorophenylmethyltriphenylphosphonium bromide

HRID 727159Notes

Reaction equation

HRID 727159 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][Br:9].[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=CC=CC=1>[Br-:9].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][P+:16]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 11905alpha-Bromo-o-chlorotoluene

Product 1

HCID 167315982-Chlorophenylmethyltriphenylphosphonium bromideYield 99.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under a nitrogen atmosphere, a solution of 10.0 grams (0.049 mole) of 2-chlorophenylmethyl bromide and 13.0 grams (0.050 mole) of triphenylphosphine in about 100 mL of toluene was heated at reflux for about 18 hours. The reaction mixture was cooled, and a solid was collected by filtration. The solid was washed with toluene and dried under vacuum, yielding 22.8 grams of 2-chlorophenylmethyltriphenylphosphonium bromide, mp>250° C.

Workup

  1. temperatureat reflux for about 18 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationa solid was collected by filtration
  4. washThe solid was washed with toluene
  5. customdried under vacuum

Sources & evidence

ORD record
ord-4c3eee68e2a840059eb02a69909134e9
Source dataset
uspto-grants-1998_01
Patent number
US05712281

Reaction notes

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