Triphenylphosphine → Phosphonium, pentadecyltriphenyl-, bromide

HRID 1720080Notes

Reaction equation

HRID 1720080 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-9f5eadf056524d93932c7409d55f4a5d
Source dataset
uspto-grants-1996_04
Patent number
US05504107

Reaction notes

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