4-Chloro-2-fluoro-N-methoxy-N-methylbenzamide → 1-(4-Chloro-2-fluorophenyl)ethan-1-one

HRID 1744875Notes

Reaction equation

HRID 1744875 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](N(OC)C)=[O:7])=[C:4]([F:14])[CH:3]=1.[CH3:15]COCC.C[Mg+].[Br-]>C(Cl)Cl>[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](=[O:7])[CH3:15])=[C:4]([F:14])[CH:3]=1

Participants

4

Reactant 2

HCID 222258304-Chloro-2-fluoro-N-methoxy-N-methylbenzamideHCID 178467672HCID 178467672, compound

Product 1

HCID 150305521-(4-Chloro-2-fluorophenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the above benzamide (1 eq) in CH2Cl2 (0.5 M) at 0° C. was added 3M/Et2O MeMgBr (1.25 eq). The reaction mixture was slowly warmed to rt over a 2 hrs period, quenched with 0.5 M aqueous citric acid and extracted with Et2O. The combined organic layers were washed with brine, dried over MgSO4 and concentrated. The residue was purified by flash chromatography on silica gel eluted with 20% EtOAc/hexane to give the title compound.

Workup

  1. customquenched with 0.5 M aqueous citric acid
  2. extractionextracted with Et2O
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel
  7. washeluted with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-59a8723bc9de48999c2aef3a4cd69602
Source dataset
uspto-grants-2006_03
Patent number
US07019022B2

Reaction notes

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