Diethylformamide → 4,4,4-Trifluorobutanoyl chloride

HRID 1198301Notes

Reaction equation

HRID 1198301 reaction equation
C(N(CC)C=O)C.[C:8](Cl)(=O)[C:9]([Cl:11])=[O:10].[F:14][C:15]([F:22])([F:21])[CH2:16]CC(O)=O>C(Cl)Cl>[F:14][C:15]([F:22])([F:21])[CH2:16][CH2:8][C:9]([Cl:11])=[O:10]

Participants

5

Reactant 3

HCID 12051DiethylformamideHCID 65578Oxalyl chlorideHCID 27770854,4,4-Trifluorobutanoic acid

Product 1

HCID 151044744,4,4-Trifluorobutanoyl chlorideYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethyl 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-d01a069ed0044da5acc9d33e5b1f0441
Source dataset
uspto-grants-1994_01
Patent number
US05280125

Reaction notes

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