Phosphine, triphenyl-, hydrobromide → Triphenyl[2-(5-phenylpentyloxy)benzyl]phosphonium bromide

HRID 1927403Notes

Reaction equation

HRID 1927403 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:19]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br-:21].[C:22]1([PH+:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(#N)C>[Br-:21].[C:35]1([P+:28]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:19][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[O:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

4

Reactant 2

HCID 517696Phosphine, triphenyl-, hydrobromideHCID 20764199[2-(5-Phenylpentyloxy)phenyl]methanol

Product 1

HCID 22560990Triphenyl[2-(5-phenylpentyloxy)benzyl]phosphonium bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 18.7 g (69.16 mmol) of [2-(5-phenylpentyloxy)phenyl]methanol in 120 ml of acetonitrile is mixed with 22.55 g (65.71 mmol) of triphenylphosphonium bromide and heated under reflux for 3 hours. The reaction solution is then concentrated to dryness. 36.6 g (61.45 mmol, 83% of theory) of crystalline product are obtained and are reacted without further purification.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. concentrationThe reaction solution is then concentrated to dryness
  4. custom36.6 g (61.45 mmol, 83% of theory) of crystalline product are obtained
  5. customare reacted without further purification

Sources & evidence

ORD record
ord-7e0374c2a6b044fd9464b6b7dec1606a
Source dataset
uspto-grants-2012_05
Patent number
US08183271B2

Reaction notes

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