Water → 1-(4,4-Difluorocyclohexyl)ethan-1-one

HRID 1527129Notes

Reaction equation

HRID 1527129 reaction equation
[F:1][C:2]1([F:12])[CH2:7][CH2:6][CH:5]([C:8](NC)=[O:9])[CH2:4][CH2:3]1.[CH3:13][Mg+].[Br-].O>C1COCC1>[F:1][C:2]1([F:12])[CH2:7][CH2:6][CH:5]([C:8](=[O:9])[CH3:13])[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 70231221HCID 70231221, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 143656631-(4,4-Difluorocyclohexyl)ethan-1-oneYield 63.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 4,4-difluoro-N-methyl cyclohexanecarboxamide (3 g, 14.5 mmol) in THF (20 mL) were added CH3MgBr (5.19 g, 43.5 mmol) in −78° C. The mixture was stirred at −78° C. for 5 hr. Water (10 mL) was added and the mixture was concentrated and extracted by CH2Cl2 (40 mL*3). The organic layer was washed with brine and dried over sodium sulfate. The organic layer was concentrated to give 1-(4,4-difluorocyclohexyl)ethanone (1.5 g, crude) for next step.

Workup

  1. concentrationthe mixture was concentrated
  2. extractionextracted by CH2Cl2 (40 mL*3)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-dd3b4ce2ad6d44e6a37e9c5ee0640e5b
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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