Oxalyl chloride → 3,4,4-Trifluoro-3-butenoyl chloride

HRID 1940838Notes

Reaction equation

HRID 1940838 reaction equation
[F:1][C:2](=[C:7]([F:9])[F:8])[CH2:3][C:4](O)=[O:5].C(Cl)(=O)C([Cl:13])=O>CN(C=O)C>[F:1][C:2](=[C:7]([F:9])[F:8])[CH2:3][C:4]([Cl:13])=[O:5]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 152391743,4,4-Trifluoro-3-butenoic acid

Product 1

HCID 109207893,4,4-Trifluoro-3-butenoyl chlorideYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A mixture of 3,4,4-trifluoro-3-butenoic acid (IV) (19.28 g, 138 mmol), oxalyl chloride (21.8 g, 172 mmol; 15 mL) and two drops of DMF was stirred for 6 hours and distilled at atmospheric pressure under nitrogen. The fraction boiling at 90°-98° C. was collected to give 16.1 g (74%) of the desired product as a clear liquid.

Workup

  1. distillationdistilled at atmospheric pressure under nitrogen
  2. customThe fraction boiling at 90°-98° C. was collected

Sources & evidence

ORD record
ord-cbf9b0c81d0445ff8574f911d204fded
Source dataset
uspto-grants-1997_12
Patent number
US05700840

Reaction notes

Loading…