Ammonium Chloride → 1-(4-Bromo-2-fluorophenyl)ethan-1-one

HRID 71086Notes

Reaction equation

HRID 71086 reaction equation
[Br: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][Mg]Br.[Cl-].[NH4+]>C1COCC1>[Br:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](=[O:7])[CH3:15])=[C:4]([F:14])[CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 532110634-Bromo-2-fluoro-N-methoxy-N-methylbenzamideHCID 178418573HCID 178418573, compound

Product 1

HCID 219385811-(4-Bromo-2-fluorophenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-bromo-2-fluoro-N-methoxy-N-methylbenzamide (13 g) in THF (4.0 mL) was added dropwise methylmagnesium bromide (3M ethylether solution, 30 mL) at 0° C., and the mixture was stirred at room temperature for 3 hr. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (10 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-25d1a90762e042d3badb475d8187a378
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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