HCID 53417458, compound → 1-(3-Bromo-4-fluorophenyl)ethan-1-one

HRID 2175804Notes

Reaction equation

HRID 2175804 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[F:14])[C:5](N(OC)C)=[O:6].[CH3:15][Mg]Cl>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:5](=[O:6])[CH3:15])[CH:11]=[CH:12][C:13]=1[F:14]

Participants

4

Reactant 2

HCID 53417458HCID 53417458, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 705081-(3-Bromo-4-fluorophenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-bromo-4-fluoro-N-methoxy-N-methylbenzamide (50 g, 0.19 mol) in 500 mL of THF was cooled to 0° C. in ice bath, and then the mixture was added MeMgCl (27.3 g, 0.21 mol) dropwise. The reaction mixture was stirred under N2 for 1 h. The reaction mixture was quenched with sat. NH4Cl and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuum. The residue was purified with silica gel column chromatography to give 1-(3-bromo-4-fluorophenyl)ethanone.

Workup

  1. customThe reaction mixture was quenched with sat. NH4Cl
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuum
  6. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-c8d9ecbe72fe43f689019c1180439c87
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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