Triphenylphosphonium bromide → [2-(2-Chlorobenzyloxy)-5-fluorobenzyl]triphenylphosphonium bromide

HRID 1921868Notes

Reaction equation

HRID 1921868 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:7]=1[CH2:8]O.[BrH:19].[C:20]1([P:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(#N)C>[Br-:19].[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:7]=1[CH2:8][P+:26]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 80811Triphenylphosphonium bromide2×HCID 578643292-(2-Chlorobenzyloxy)-5-fluorobenzyl alcohol

Product 1

HCID 86634289[2-(2-Chlorobenzyloxy)-5-fluorobenzyl]triphenylphosphonium bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4.60 g (17 mmol) of 2-(2-chlorobenzyloxy)-5-fluorobenzyl alcohol are dissolved in 10 ml of acetonitrile, then 5.62 g (16 mmol) of triphenylphosphine hydrobromide are added, and the suspension is stirred under reflux for 12 h. A further 2.80 g (8 mmol) of triphenylphosphine hydrobromide are added, and the mixture is stirred under reflux for a further 3 h. The solvent is mostly distilled out in vacuo, the crystals which have separated out are stirred with petroleum ether, filtered off with suction and dried on a clay dish. 9.82 g (15.7 mmol, 92% of theory) of the title compound are obtained.

Workup

  1. temperatureunder reflux for 12 h
  2. stirringthe mixture is stirred
  3. temperatureunder reflux for a further 3 h
  4. distillationThe solvent is mostly distilled out in vacuo
  5. customthe crystals which have separated out
  6. stirringare stirred with petroleum ether
  7. filtrationfiltered off with suction
  8. customdried on a clay dish

Sources & evidence

ORD record
ord-f099c4c3604a45d9a237cfcf4addd789
Source dataset
uspto-grants-2012_05
Patent number
US08173704B2

Reaction notes

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