Thionyl Chloride → (2E)-3-(3-Fluorophenyl)-2-propenoyl chloride

HRID 1448113Notes

Reaction equation

HRID 1448113 reaction equation
[F: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>[F: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 1551219(2E)-3-(3-Fluorophenyl)-2-propenoic acid

Product 1

HCID 5706470(2E)-3-(3-Fluorophenyl)-2-propenoyl chlorideYield 94.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of trans 3-fluorocinnamic acid (32.3 g), thionyl chloride (48 g) and dry benzene (300 ml) was heated at reflux for 2 hours. Solvent and excess thionyl chloride was removed by distillation at reduced pressure leaving trans 3-fluorocinnamoyl chloride (34 g) as the oil.

Workup

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

Sources & evidence

ORD record
ord-3d7e39f874674a269d87ab9d5cadac39
Source dataset
uspto-grants-1979_12
Patent number
US04179524

Reaction notes

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