Triphenylphosphine → (5-Carboxypentyl)triphenylphosphanium bromide

HRID 2386191Notes

Reaction equation

HRID 2386191 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[C:10]1([P:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(#N)C>[Br-:1].[C:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][P+:16]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 202106-Bromohexanoic acid

Product 1

HCID 2779280(5-Carboxypentyl)triphenylphosphanium bromideYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 6-bromohexanoic acid (10.00 g, 51.27 mmol) and triphenyl phosphine (14.12 g, 53.83 mmol) in freshly distilled acetonitrile (50 mL) was vigorously stirred and refluxed for 48 hours. The solution was allowed to come to ambient temperature and the Wittig salt was precipitated upon scratching the inside wall of the glass reaction vessel with a spatula. The white solid product was collected, washed with ether and filtered to provide the title compound in 98% yield (22.87 g): 1H NMR (400 MHz, CD3OD) δ 1.62-1.72 (m, 6H), 2.29 (t, 2H), 3.40-3.47 (m, 2H), 7.76-7.91 (m, 15H).

Workup

  1. temperaturerefluxed for 48 hours
  2. customto come to ambient temperature
  3. customthe Wittig salt was precipitated
  4. customthe inside wall of the glass reaction vessel with a spatula
  5. customThe white solid product was collected
  6. washwashed with ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-a5586063e3e74873b4c72e605e6198b8
Source dataset
uspto-grants-2012_09
Patent number
US08268817B2

Reaction notes

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