Ethyl trifluoroacetate → 4,4,4-Trifluoro-1-(4-fluorophenyl)butane-1,3-dione

HRID 1897157Notes

Reaction equation

HRID 1897157 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.C[O-].[Na+].[CH3:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)=[O:15]>C(OC)(C)(C)C.Cl>[F:9][C:2]([F:1])([F:8])[C:3](=[O:5])[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)=[O:15]

Participants

6

Reactant 3

HCID 9794Ethyl trifluoroacetateHCID 98284'-FluoroacetophenoneHCID 10942334Sodium Methoxide

Product 1

HCID 27714764,4,4-Trifluoro-1-(4-fluorophenyl)butane-1,3-dioneYield 97%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of ethyl trifluoroacetate (23.9 mL, 199 mmol) in tertbutylmethylether (230 mL) containing sodium methoxide (5.4 M, 39.6 mL, 214 mmol) was added 4-fluoroacetophenone (25 g, 181 mmol) and the resulting mixture stirred at room temperature for 3 h and then poured into ice-water. The mixture was then diluted with HCl (2 N, 200 mL) and then extracted with ethyl acetate. The combined organic extracts were then dried over sodium sulfate and evaporated to afford the title compound (40.9 g, 97%) which was obtained as an orange oil. MS: m/e=232.9 [M−H]−.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic extracts were then dried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-10a7d13f6e2141f0bfc0e6257ecf1133
Source dataset
uspto-grants-2013_08
Patent number
US08518974B2

Reaction notes

Loading…