Hydrochloric Acid → 1-(2-Fluoro-3-trifluoromethyl-phenyl)-3-phenyl-propan-1-one

HRID 643337Notes

Reaction equation

HRID 643337 reaction equation
[F:1][C:2]1[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][C:3]=1[C:4](N(OC)C)=[O:5].[CH2:18]([Mg]Cl)[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl>C1COCC1>[F:1][C:2]1[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][C:3]=1[C:4](=[O:5])[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11196047Benzamide, 2-fluoro-N-methoxy-N-methyl-3-(trifluoromethyl)-HCID 178418865HCID 178418865, compound

Product 1

HCID 685793531-(2-Fluoro-3-trifluoromethyl-phenyl)-3-phenyl-propan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) solution of 2-fluoro-N-methoxy-N-methyl-3-trifluoromethyl-benzamide (5.0 g, 20 mmol) in THF (50 ml) was added phenethyl magnesium chloride (50 ml of 1.0M in THF) and the reaction was warmed to r.t. After 2 hr, the reaction was poured into 2N HCl and extracted with ether. The organic layer was dried (MgSO4), and concentrated and the product was purified by column chromatography (eluent 5% EtOAc/Hexane) to give 1-(2-fluoro-3-trifluoromethyl-phenyl)-3-phenyl-propan-1-one as a clear oil (4.8 g). MS (ES) m/z 297.0.

Workup

  1. extractionextracted with ether
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customthe product was purified by column chromatography (eluent 5% EtOAc/Hexane)

Sources & evidence

ORD record
ord-b070f02e9a294296b7a02f863db36a6b
Source dataset
uspto-grants-2010_04
Patent number
US07700595B2

Reaction notes

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