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

HRID 1288216Notes

Reaction equation

HRID 1288216 reaction equation
[Br:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].[C:7]1([P:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(#N)C>[Br-:1].[C:4]([CH2:3][CH2:2][P+:13]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)([OH:6])=[O:5]

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 mixture of 3-bromopropionic acid (50 g.), triphenylphosphine (85.8 g.) and acetonitrile (250 ml.) is heated under reflux for 23 hrs. and then 166 ml. of acetonitrile is removed by distillation. After cooling the remaining solution to room temperature, benzene (250 ml.) is added and the mixture is allowed to stand for 16 hrs. The solid which separates is removed by filtration to give 120.5 g. of the title compound, m.p. 197°-200°; infrared absorptions at 2900, 2610, 2540, 1745, 1620, 1585, 1485, 1435, 1385, 1325, 1230, 1110, 750, 725 and 690 cm-1 ; NMR peaks at 2.7-3.3 (broad), 3.5-4.2 (broad) and 7.6-7.9 (multiplet) δ.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 23 hrs
  3. customof acetonitrile is removed by distillation
  4. additionbenzene (250 ml.) is added
  5. customThe solid which separates is removed by filtration
  6. customto give 120.5 g

Sources & evidence

ORD record
ord-6d65f9d2dc874d36a3b936f67021e4bc
Source dataset
uspto-grants-1976_10
Patent number
US03987087

Reaction notes

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