3-Bromopropionic acid → (2-Carboxyethyl)triphenylphosphonium bromide

HRID 1579730Notes

Reaction equation

HRID 1579730 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24]>C(#N)C>[Br-:20].[C:23]([CH2:22][CH2:21][P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([OH:25])=[O:24]

Participants

4

Reactant 2

HCID 115533-Bromopropionic acidHCID 11776Triphenylphosphine

Product 1

HCID 2733850(2-Carboxyethyl)triphenylphosphonium bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 90 g. (0.343 mole) of triphenylphosphine and 50 g. (0.326 mole) of 3-bromopropionic acid in 550 ml. of acetonitrile was refluxed for two days. The reaction mixture was then distilled under reduced pressure to remove acetonitrile, and the residue was stirred well together with diethyl ether, and then the upper ethereal layer removed by decantation. The operation was repeated twice to form the crystalline product, which was recrystallised from acetonitrile; yield of the title compound: 115 g, m.p. 195°-198°C. Infra-red (hereinafter abbreviated to IR) absorption spectrum (potassium bromide tablet): 2880, 1740, 1434, 1382, 1322, 1230, 1105, 745, 690, 520 and 505 cm-1.

Workup

  1. distillationThe reaction mixture was then distilled under reduced pressure
  2. customto remove acetonitrile
  3. customthe upper ethereal layer removed by decantation
  4. customto form the crystalline product, which
  5. customwas recrystallised from acetonitrile
  6. customInfra-red (hereinafter abbreviated to IR) absorption spectrum (potassium bromide tablet)

Sources & evidence

ORD record
ord-03082a70860b490f874354bfaded209c
Source dataset
uspto-grants-1976_01
Patent number
US03931296

Reaction notes

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