Dimethylformamide → 4,4,4-Trifluorobutanoyl chloride

HRID 1975428Notes

Reaction equation

HRID 1975428 reaction equation
CN(C)C=O.[C:6](Cl)(=O)[C:7]([Cl:9])=[O:8].[F:12][C:13]([F:20])([F:19])[CH2:14]CC(O)=O>C(Cl)Cl>[F:12][C:13]([F:20])([F:19])[CH2:14][CH2:6][C:7]([Cl:9])=[O:8]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 27770854,4,4-Trifluorobutanoic acid

Product 1

HCID 151044744,4,4-Trifluorobutanoyl chlorideYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dimethyl formamide (1.0 mL) and oxalylchloride (239 mL) were added to a 0° C. solution of 4,4,4-trifluorobutyric acid (343 g) in dry methylene chloride (230 mL) and warmed to room temperature overnight. The methylene chloride was removed by distillation and the residue distilled to yield 4,4,4-trifluorobutyryl chloride (328 g, 85%); bp 103°-106° C.; partial NMR (300 MHz, CDCl3): 2.47-2.64 (m, 2H, CF3CH2) 3.19 (t, H, CH2COCl).

Workup

  1. customThe methylene chloride was removed by distillation
  2. distillationthe residue distilled

Sources & evidence

ORD record
ord-2547e74275dd49a79c2804f60b64995d
Source dataset
uspto-grants-1994_02
Patent number
US05286740

Reaction notes

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