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

HRID 1257795
Notes
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Reaction equation

HRID 1257795 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.[OH2:16]>CS(C)=O>[F:14][C:6]1[CH:5]=[C:4]([C:1](=[O:3])[CH:2]=[O:16])[CH:13]=[CH:12][C:7]=1[C:8]([O:10][CH3:11])=[O:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 59216348Methyl 4-acetyl-2-fluorobenzoate

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 4-acetyl-2-fluorobenzoate (1.6 g, 8.2 mmol) and 8.8M hydrogen bromide in water (2.8 mL) in dimethyl sulfoxide (20 mL) was stirred at 60° C. overnight. After cooling, the mixture was poured into ice-water. The reaction mixture was extracted with diethyl ether. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated to yield the desired product which was used in the next reaction step without further purification. (1.60 g, 93.3%).

Workup

  1. temperatureAfter cooling
  2. extractionThe reaction mixture was extracted with diethyl ether
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-273427fe1bd0467eb4e09a53638233c8
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08461330B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes