4-Bromo-3-fluoro-N-methoxy-N-methylbenzamide → 1-(4-Bromo-3-fluorophenyl)butan-1-one

HRID 965978Notes

Reaction equation

HRID 965978 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](N(OC)C)=[O:7])=[CH:4][C:3]=1[F:14].[CH2:15]([Mg]Br)[CH2:16][CH3:17]>O1CCCC1>[Br:1][C:2]1[CH:13]=[CH:12][C:5]([C:6](=[O:7])[CH2:15][CH2:16][CH3:17])=[CH:4][C:3]=1[F:14]

Participants

4

Reactant 2

HCID 223138234-Bromo-3-fluoro-N-methoxy-N-methylbenzamideHCID 178455851HCID 178455851, compound

Product 1

HCID 223138401-(4-Bromo-3-fluorophenyl)butan-1-oneYield 81.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 4-Bromo-3-fluoro-N-methoxy-N-methylbenzamide (3.0 g, 12.19 mmol) in tetrahydrofuran (35 ml) was added 2M n-propylmagnesium bromide (12.2 ml, 24.38 mmol) dropwise under nitrogen at 0° C. The reaction mixture was stirred at room temperature for 2 h. This was quenched by sat. ammonium chloride and stirred at rt for 30 min. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The extracts was dried (MgSO4) and concentrated. This was purified on silica gel eluting with ethyl acetate/hexane (1:10) to afford 2.44 g (81.7%) of the titled compound as a slight yellow oil.

Workup

  1. customThis was quenched by sat. ammonium chloride
  2. stirringstirred at rt for 30 min
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. dry with materialThe extracts was dried (MgSO4)
  6. concentrationconcentrated
  7. customThis was purified on silica gel eluting with ethyl acetate/hexane (1:10)

Sources & evidence

ORD record
ord-9bbc321a1af34c72b0bf2f34c9eea19e
Source dataset
uspto-grants-2005_10
Patent number
US06951876B2

Reaction notes

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