Triphenylphosphine → (4-Carboxybutyl)triphenylphosphonium bromide

HRID 478734Notes

Reaction equation

HRID 478734 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].[C:9]1([P:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(#N)C>[Br-:1].[C:6]([CH2:5][CH2:4][CH2:3][CH2:2][P+:15]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 163685-Bromovaleric acid

Product 1

HCID 161236(4-Carboxybutyl)triphenylphosphonium bromideYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-bromopentanoic acid (6.9 g, 38 mmol) and triphenylphosphine (10 g, 38 mmol) in dry acetonitrile (30 ml) was heated under reflux overnight. Evaporation of solvent yielded crystals. The resultant crystals were washed with a small amount of acetonitrile and dried at room temperature under reduced pressure to afford a target product, (4-carboxybutyl)-triphenylphosphonium bromide (14.6 g, 87%), which was used in the next step without any further treatment.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customEvaporation of solvent
  4. customyielded crystals
  5. washThe resultant crystals were washed with a small amount of acetonitrile
  6. customdried at room temperature under reduced pressure

Sources & evidence

ORD record
ord-d3f90a85cbc14dbe8b2ea5eb42b4ea5e
Source dataset
uspto-grants-2003_11
Patent number
US06642250B2

Reaction notes

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