Thionyl Chloride → (E)-4-Fluorocinnamoyl chloride

HRID 2352315Notes

Reaction equation

HRID 2352315 reaction equation
[F: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>C1(C)C=CC=CC=1>[F: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

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 15302344-Fluorocinnamic acid

Product 1

HCID 5706471(E)-4-Fluorocinnamoyl chlorideYield 105.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 15.0 g. (0.09 mole) of trans-4-fluorocinnamic acid (Compound LXXVI) and 30 ml. (0.41 mole) of thionyl chloride in 100 ml. of toluene is stirred at 70° C. for 18 hours, and the solvent is evaporated at reduced pressure to obtain the crude product (17.5 g. (>100%)).

Workup

  1. additionA mixture of 15.0 g
  2. customthe solvent is evaporated at reduced pressure

Sources & evidence

ORD record
ord-776ffac4160a49d59cd8051d63e04376
Source dataset
uspto-grants-1989_10
Patent number
US04876280

Reaction notes

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