Thionyl Chloride → Bromophenylacetyl chloride

HRID 465643Notes

Reaction equation

HRID 465643 reaction equation
[Br:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3](O)=[O:4].S(Cl)([Cl:14])=O>>[Br:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([Cl:14])=[O:4]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 97919Bromo(phenyl)acetic acid

Product 1

HCID 598182Bromophenylacetyl chlorideYield 100%

Conditions

Temperature
25 °C

Procedure

A solution of α-bromophenylacetic acid (19.3 g, 89.7 mmol) in thionylchloride (100 mL) was refluxed (2 hours), cooled (25° C.), and stirred (25° C., 14 hours). The resulting solution was concentrated in vacuo, diluted with ether, and concentrated again to yield 21.0 g (100%) of α-bromophenylacetylchloride as a slightly yellow oil which was used without further purification.

Workup

  1. concentrationThe resulting solution was concentrated in vacuo
  2. additiondiluted with ether
  3. concentrationconcentrated again

Sources & evidence

ORD record
ord-8a43d18c5a0146cd91aa57ee27c5696d
Source dataset
uspto-grants-1992_10
Patent number
US05153226

Reaction notes

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