Hydrochloric Acid → 4,4,4-Trifluoro-1-(4-fluorophenyl)butane-1,3-dione

HRID 1994278Notes

Reaction equation

HRID 1994278 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([O:5]CC)=O.C[O-].[Na+].[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=1.Cl>C(OC)(C)(C)C>[F:9][C:2]([F:1])([F:8])[C:3](=[O:5])[CH2:21][C:20]([C:17]1[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=1)=[O:22]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9794Ethyl trifluoroacetateHCID 98284'-FluoroacetophenoneHCID 10942334Sodium Methoxide

Product 1

HCID 27714764,4,4-Trifluoro-1-(4-fluorophenyl)butane-1,3-dioneYield 823.3%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

Ethyl trifluoroacetate (2.35 g, 1.66 mmol) was placed in a 50 mL round bottom flask, and dissolved in methyl tert-butyl ether (7.5 mL). To the stirred solution was added 25 weight % sodium methoxide (4.0 mL, 17.7 mmol) via an addition funnel over a 2 minute period. Next, 4′-fluoroacetophenone (2.1 g, 15 mmol) was dissolved in methyl tert-butyl ether (2 mL), and added to the reaction dropwise over 5 minutes. After stirring overnight (15.75 hours), 3N HCl (7.0 mL) was added. The organic layer was collected, washed with brine (7.5 mL), dried over MgSO4, filtered, and concentrated in vacuo to give 3.2 g of pale-orange solid. The solid was recrystallized from iso-octane to give 2.05 g of the dione.

Workup

  1. additionadded to the reaction dropwise over 5 minutes
  2. additionwas added
  3. customThe organic layer was collected
  4. washwashed with brine (7.5 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-763cbc3217884b9abb0561357ed92a22
Source dataset
uspto-grants-2010_01
Patent number
US07652149B2

Reaction notes

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