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

HRID 607605Notes

Reaction equation

HRID 607605 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-f55fead6550c4dcd8c1399cc4480f337
Source dataset
uspto-grants-2011_03
Patent number
US07915408B2

Reaction notes

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