Triphenylphosphine → 12-Methyl-11-tridecenyl-triphenylphosphonium Bromide

HRID 622118Notes

Reaction equation

HRID 622118 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14].[C:16]1([P:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(#N)C>[Br-:1].[CH3:14][C:13]([CH3:15])=[CH:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][P+:22]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 212937251-Bromo-12-methyl-11-tridecene

Product 1

HCID 2129372712-Methyl-11-tridecenyl-triphenylphosphonium Bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Bromo-12-methyl-11-tridecene (4.4 g, 16 mmoles) and triphenylphosphine (4.65 g, 17 mmoles) dissolved in acetonitrile (80 ml) were heated to reflux for 4 days, cooled and concentrated in vacuo. The residue was chromatographed on silica gel eluted with chloroform and then with methanol-chloroform (2:3). Fractions containing the product were concentrated in vacuo, triturated with ether, filtered and dried in vacuo to afford the desired phosphonium salt.

Workup

  1. temperaturewere heated
  2. temperatureto reflux for 4 days
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel
  6. washeluted with chloroform
  7. additionFractions containing the product
  8. concentrationwere concentrated in vacuo
  9. customtriturated with ether
  10. filtrationfiltered
  11. customdried in vacuo

Sources & evidence

ORD record
ord-d27479dc65674ab59cc4d7907eef6fa5
Source dataset
uspto-grants-1988_09
Patent number
US04769386

Reaction notes

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