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

HRID 1099087Notes

Reaction equation

HRID 1099087 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-0638f7e87f224bdb8fc8394a9c2ed691
Source dataset
uspto-grants-2012_03
Patent number
US08143251B2

Reaction notes

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