Hydrochloric Acid → 4,4-Difluoro-1-(4-trifluoromethylphenyl)butane-1,3-dione

HRID 441045Notes

Reaction equation

HRID 441045 reaction equation
[F:1][CH:2]([F:8])[C:3]([O:5]CC)=O.C[O-].[Na+].[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=1.Cl>CCOCC.C1COCC1>[F:8][CH:2]([F:1])[C:3](=[O:5])[CH2:21][C:20]([C:17]1[CH:18]=[CH:19][C:14]([C:13]([F:12])([F:23])[F:24])=[CH:15][CH:16]=1)=[O:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9961Ethyl difluoroacetateHCID 697311-(4-(Trifluoromethyl)phenyl)ethan-1-oneHCID 10942334Sodium Methoxide

Product 1

HCID 189203694,4-Difluoro-1-(4-trifluoromethylphenyl)butane-1,3-dioneYield 91%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl difluoroacetate (2.78 g, 22.4 mmol) was placed in a 100 mL round bottom flask and dissolved in ether (10 mL). To the stirred solution was added 25 weight % sodium methoxide (6.02 g, 27.8 mmol ) followed by 4'-(trifluoromethyl)acetophenone (3.80 g, 20.2 mmol) and THF (20 mL). The reaction was stirred at room temperature overnight (15.6 hours), then treated with 3N HCl (20 mL). The organic layer was collected and washed with brine, dried over MgSO4, concentrated in vacuo to give a brown oil (4.88 g, 91%). 1H NMR (acetone d6) 300 MHz 15.10 (br s, 1H), 8.03 (d, J=8.7 Hz, 2H), 7.77 (d, J=8.5 Hz, 2H), 6.59 (s, 1H), 6.02 (t, J=54.2 Hz, 1H); 19F NMR (acetone d6) 300 MHz: - 63.70 (s), -127.10 (d); M+ 266.

Workup

  1. customThe organic layer was collected
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3a64f12d4b7e40fb8ab75863936a3cf7
Source dataset
uspto-grants-1996_05
Patent number
US05521207

Reaction notes

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