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

HRID 2262551Notes

Reaction equation

HRID 2262551 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]>CC(OC)(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 TBME (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-52236ad3321d4644a1feca1f9b008fc9
Source dataset
uspto-grants-2010_12
Patent number
US07851469B2

Reaction notes

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