Triphenylphosphine → Phosphonium, (5-hydroxypentyl)triphenyl-, bromide

HRID 2172352Notes

Reaction equation

HRID 2172352 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].[C:8]1([P:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(O)C>[Br-:1].[OH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][P+:14]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 1187091-Pentanol, 5-bromo-

Product 1

HCID 2784772Phosphonium, (5-hydroxypentyl)triphenyl-, bromide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An equivalent of 5-bromopentanol and an equivalent of triphenylphosphine in refluxed ethanol are placed in a flask. After 72 hours of agitation in these conditions, and once returned to ambient temperature, the ethanol is evaporated under vacuum and the residue is placed into toluene at 4° C. overnight. The (5-hydroxypentyl)triphenylphosphonium bromide formed is filtered on a frit, rinsed with methyl tert-butyl ether then dried under vacuum.

Workup

  1. customonce returned to ambient temperature
  2. customthe ethanol is evaporated under vacuum
  3. waitthe residue is placed into toluene at 4° C. overnight

Sources & evidence

ORD record
ord-a220f2c9520343af94c86a165878c8c8
Source dataset
uspto-grants-2015_06
Patent number
US09051531B2

Reaction notes

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