Thionyl Chloride → 6,6-Difluorohex-5-enoic acid chloride

HRID 6469Notes

Reaction equation

HRID 6469 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]([F:14])=[CH:7][CH2:8][CH2:9][CH2:10][C:11](O)=[O:12]>CN(C)C=O>[F:5][C:6]([F:14])=[CH:7][CH2:8][CH2:9][CH2:10][C:11]([Cl:3])=[O:12]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 112980566,6-difluorohex-5-enoic Acid

Product 1

HCID 197938396,6-Difluorohex-5-enoic acid chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.23 ml (140.68 mmol) Thionyl chloride was added dropwise to 8.0 g (52.29 mmol) of the product of Example 9 at room temperature. A drop of dimethylformamide was added and the mixture heated under reflux for 6 hours. It was then distilled under reduced pressure.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 6 hours
  3. distillationIt was then distilled under reduced pressure

Sources & evidence

ORD record
ord-d30cf53005b044ea9db9fca6b67dce41
Source dataset
uspto-grants-1993_09
Patent number
US05248810

Reaction notes

Loading…