Hydrogen Bromide → Methyl 2-fluoro-4-(oxoacetyl)benzoate
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]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- temperatureAfter cooling
- extractionThe reaction mixture was extracted with diethyl ether
- washThe combined organic extracts were washed with brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-273427fe1bd0467eb4e09a53638233c8
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08461330B2
Reaction notes
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