Benzamide, 2-fluoro-N-methoxy-N-methyl-3-(trifluoromethyl)- → (2-Fluoro-3-trifluoromethyl-phenyl)-(4-methoxy-phenyl)-methanone

HRID 735405Notes

Reaction equation

HRID 735405 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([Mg]Br)=[CH:5][CH:4]=1.[F:11][C:12]1[C:23]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:21]=[CH:20][C:13]=1[C:14](N(OC)C)=[O:15]>C1COCC1>[F:11][C:12]1[C:23]([C:24]([F:26])([F:27])[F:25])=[CH:22][CH:21]=[CH:20][C:13]=1[C:14]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:15]

Participants

4

Reactant 2

HCID 11196047Benzamide, 2-fluoro-N-methoxy-N-methyl-3-(trifluoromethyl)-HCID 178491912HCID 178491912, compound

Product 1

HCID 11231817(2-Fluoro-3-trifluoromethyl-phenyl)-(4-methoxy-phenyl)-methanoneYield 90.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1 milliliter of a 1M THF solution of 4-methoxyphenylmagnesium bromide (1 mmol) was added to a solution of 126 mg (0.5 mmol) of 2-fluoro-N-methoxy-N-methyl-3-trifluoromethyl-benzamide in 2 ml of THF at 0° C. The reaction mixture was stirred for 2 hrs. at this temperature and then quenched with saturated NH4Cl solution and the phases were separated. The aqueous phase was extracted twice with CH2Cl2 and the combined organic phases were washed with brine and dried over Na2SO4. The resulting ketone (135 mg) was obtained after flash chromatographic purification using 5% EtOAc in heptane as an eluent.

Workup

  1. customat this temperature and then quenched with saturated NH4Cl solution
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted twice with CH2Cl2
  4. washthe combined organic phases were washed with brine
  5. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-5ea0e97535e34433b92836de30b527a4
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

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