Thionyl Chloride → 3-(4-Bromophenyl)prop-2-enoyl chloride

HRID 1067228Notes

Reaction equation

HRID 1067228 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8](O)=[O:9])=[CH:4][CH:3]=1.S(Cl)([Cl:15])=O>>[Br:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([Cl:15])=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 99777p-Bromocinnamic acid

Product 1

HCID 534112933-(4-Bromophenyl)prop-2-enoyl chloride

Procedure

A solution of 4-bromocinnamic acid (5.03 g, 22.2 mmol) in thionyl chloride (SOCl2) (15 mL) was stirred at 23° C. for 16 h, and then heated at reflux for a further 2 h. The solvents were evaporated in vacuo and the residue azeotroped with toluene (×3) to yield 4-bromocinnamoyl chloride as an orange-brown solid in quantitative yield.

Workup

  1. temperatureheated
  2. temperatureat reflux for a further 2 h
  3. customThe solvents were evaporated in vacuo
  4. customthe residue azeotroped with toluene (×3)

Sources & evidence

ORD record
ord-2e3b41211b3343b4a8b4f6727e9ae6c1
Source dataset
uspto-grants-2001_06
Patent number
US06248738B1

Reaction notes

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