Acetic Acid → 4-(2,4-Difluorophenyl)-1,1,1-trifluoro-4-hydroxy-3-buten-2-one

HRID 1440124Notes

Reaction equation

HRID 1440124 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[F:12][C:13]([F:20])([F:19])[C:14](OCC)=[O:15].C[O-].[Na+].CO.C(O)(=O)C>C(OCC)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:11])=[CH:10][C:14](=[O:15])[C:13]([F:20])([F:19])[F:12]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 887MethanolHCID 9794Ethyl trifluoroacetateHCID 677702,4-DifluoroacetophenoneHCID 10942334Sodium Methoxide

Product 1

HCID 699347784-(2,4-Difluorophenyl)-1,1,1-trifluoro-4-hydroxy-3-buten-2-oneYield 97.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 40.0 g (0.256 moles) 2',4'-difluoroacetophenone (commercially available) in 400 mL diethyl ether at 0° C. was added 40 mL (0.405 moles) ethyl trifluoroacetate. At 5° C., 80 mL of a 25% wt. sodium methoxide in methanol (0.37 moles) were added over 15 minutes. The reaction mixture was stirred overnight at 25° C. The mixture was poured over 300 mL ice water and 21.3 mL (0.37 moles) acetic acid were added. The organic layer was washed two times with water, dried over anhydrous MgSO4, and concentrated in vacuo to give 62.85 g (97%) 4-(2,4-difluorophenyl)-1,1,1-trifluoro-4-hydroxy-3-buten-2-one as a yellow oil; 1HNMR (CDCl3) ppm: 6.61 (s,1H), 6.87 (m, 1H)., 6.97 (m, 1H), 7.97 (m, 1H).

Workup

  1. additionwere added
  2. washThe organic layer was washed two times with water
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ce1c43850534496baa6781f7002c1305
Source dataset
uspto-grants-1996_03
Patent number
US05496956

Reaction notes

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