Diethyl Ether → (2-Fluoro-3-trifluoromethyl-phenyl)-(4-fluoro-phenyl)-methanone

HRID 735437Notes

Reaction equation

HRID 735437 reaction equation
CCOCC.[F:6][C:7]1[CH:12]=[CH:11][C:10]([Mg]Br)=[CH:9][CH:8]=1.[F:15][C:16]1[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][C:17]=1[C:18](N(OC)C)=[O:19]>C1COCC1>[F:15][C:16]1[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][CH:25]=[CH:24][C:17]=1[C:18]([C:10]1[CH:11]=[CH:12][C:7]([F:6])=[CH:8][CH:9]=1)=[O:19]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11196047Benzamide, 2-fluoro-N-methoxy-N-methyl-3-(trifluoromethyl)-HCID 178418676HCID 178418676, compound

Product 1

HCID 25149910(2-Fluoro-3-trifluoromethyl-phenyl)-(4-fluoro-phenyl)-methanoneYield 0.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

2M Et2O solution of 4-fluorophenylmagnesium bromide (32.5 ml; 65 mmol) was added to a solution of 12.8 g (65 mmol) of 2-fluoro-N-methoxy-N-methyl-3-trifluoromethyl-benzamide in 150 ml of THF at 0° C. The reaction mixture was heated overnight at 50° C. The reaction mixture was partitioned with EtOAc and H2O. The organic phases were washed with brine and dried over Na2SO4. The resulting ketone (135 mg) was obtained after flash chromatographic purification using hexane/CH2Cl2 (3:1, v/v) as an eluent.

Workup

  1. customThe reaction mixture was partitioned with EtOAc and H2O
  2. washThe organic phases were washed with brine
  3. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-cd92e81c71814ccc840fd109da55a50a
Source dataset
uspto-grants-2009_09
Patent number
US07592363B2

Reaction notes

Loading…