Triphenylphosphine → Phosphonium, pentadecyltriphenyl-, bromide

HRID 2257228Notes

Reaction equation

HRID 2257228 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:17]1([P:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(#N)C>[Br-:1].[CH2:2]([P+:23]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 123941-Bromopentadecane

Product 1

HCID 10392879Phosphonium, pentadecyltriphenyl-, bromideYield 99.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
135 °C

Procedure

Under nitrogen atmosphere 1-bromopentadecane (6.5 g, 22.4 mmol) was treated with 5.87 g (22.4 mmol) of triphenylphosphine in 15 mL of acetonitrile and heated to 135° C. The reaction was monitored by TLC (salt formation, about 18 hours), and the mixture was dried under reduced pressure (24 hours) to ensure removal of traces of acetonitrile and provided 12.3 g of a colorless solid which was utilized in the next reaction without further purification.

Workup

  1. customwas monitored by TLC (salt formation, about 18 hours)
  2. customthe mixture was dried under reduced pressure (24 hours)
  3. customremoval of traces of acetonitrile

Sources & evidence

ORD record
ord-2bd0da3b7b37487197d71d10c53c21f9
Source dataset
uspto-grants-1997_08
Patent number
US05656662

Reaction notes

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