Triphenylphosphine → Triphenyl(tridecyl)phosphonium bromide

HRID 867404Notes

Reaction equation

HRID 867404 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][CH3:14].[C:15]1([P:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(OCC)C>[Br-:1].[CH2:2]([P+:21]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 130001-Bromotridecane

Product 1

HCID 11124240Triphenyl(tridecyl)phosphonium bromide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 1-bromotridecane (100 g, 0.4 mol) and triphenyl phosphine (100 g, 0.4 mol) in 500 ml of xylenes was refluxed overnight. The reaction mixture was then cooled to room temperature and poured into diethyl ether. The resulting oil was washed three times with ether, dissolved in methylene chloride and then concentrated in vacuo. The oil was left standing in diethyl ether at 0° C. overnight and then concentrated in vacuo to give a white solid.

Workup

  1. washThe resulting oil was washed three times with ether
  2. dissolutiondissolved in methylene chloride
  3. concentrationconcentrated in vacuo
  4. waitThe oil was left
  5. concentrationconcentrated in vacuo
  6. customto give a white solid

Sources & evidence

ORD record
ord-322061d800534edbb6e4f0fdcbbcb9bb
Source dataset
uspto-grants-1988_10
Patent number
US04775662

Reaction notes

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