Hydrogen Bromide → Methyl 2-fluoro-4-(oxoacetyl)benzoate

HRID 2245987Notes

Reaction equation

HRID 2245987 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[C:6]([F:14])[CH:5]=1)(=[O:3])[CH3:2].Br.CS(C)=[O:18]>>[F:14][C:6]1[CH:5]=[C:4]([C:1](=[O:3])[CH:2]=[O:18])[CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 679Dimethyl SulfoxideHCID 59216348Methyl 4-acetyl-2-fluorobenzoate

Product 1

HCID 59216303Methyl 2-fluoro-4-(oxoacetyl)benzoate

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 4-acetyl-2-fluorobenzoate (1.6 g, 0.0082 mol), 48% of hydrogen bromide aqueous solution (2.8 mL) in dimethyl sulfoxide (20 mL) was stirred at 60° C. overnight. After cooling, the mixture was poured into ice-water. The product was extracted with ethyl ether. The combined extracts were washed with brine; dried over Na2SO4, filtered concentrated to yield 1.60 g of the product which was directly used in the next step without further purification.

Workup

  1. temperatureAfter cooling
  2. extractionThe product was extracted with ethyl ether
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a6ead5cee33347d0b9bdd4548d797363
Source dataset
uspto-grants-2010_03
Patent number
US07683060B2

Reaction notes

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