Thionyl Chloride → trans 3-Bromocinnamoyl chloride

HRID 1449389Notes

Reaction equation

HRID 1449389 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)/[CH:5]=[CH:6]/[C:7](O)=[O:8].S(Cl)([Cl:15])=O>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)/[CH:5]=[CH:6]/[C:7]([Cl:15])=[O:8]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 776461m-Bromocinnamic acid

Product 1

HCID 14959106trans 3-Bromocinnamoyl chlorideYield 99%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of trans 3-bromocinnamic acid (m.p. 177°-179° C.; 11.4 g), thionyl chloride (11.9 g) and dry benzene (150 ml) was heated at reflux for 2 hours. Solvent and excess thionyl chloride were removed by distillation under reduced pressure leaving trans 3-bromocinnamoyl chloride (12.2 g), b.p. 100°-100.5° C./0.2 mm Hg.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customSolvent and excess thionyl chloride were removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-0ca2dd6f06434b0f90213e6691495467
Source dataset
uspto-grants-1980_02
Patent number
US04190674

Reaction notes

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