Ethanol → Ethyl 2-bromo-4-(trifluoromethyl)benzoate
Reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH2:20](O)[CH3:21]>>[Br:1][C:2]1[CH:10]=[C:9]([C:11]([F:12])([F:13])[F:14])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:20][CH3:21])=[O:5]Participants
4
Procedure
238 g (0.885 mol) of 2-bromo-4-(trifluoromethyl)benzoic acid, 1000 ml of absolute ethanol and 100 ml of concentrated sulfuric acid are introduced successively into a 2-liter round-bottomed flask. The reaction mixture is brought to reflux for 6 hours and then poured, after cooling, onto 2.5 liters of ice-cold water; the oil formed is extracted with ethyl acetate. The organic phase is successively washed with water, with 1N sodium hydroxide solution and then again with water. After drying over magnesium sulfate, the solvent is evaporated to provide 263 g (yield: 100%) of ethyl 2-bromo-4-(trifluoromethyl)benzoate in the form of a yellow oil.
Workup
- temperatureto reflux for 6 hours
- additionpoured
- customthe oil formed
- extractionis extracted with ethyl acetate
- washThe organic phase is successively washed with water, with 1N sodium hydroxide solution
- dry with materialAfter drying over magnesium sulfate
- customthe solvent is evaporated
Sources & evidence
- ORD record
- ord-bb6e42ca444748fd9e19e6039f031dd1
- Source dataset
- uspto-grants-1996_05
- Patent number
- US05514719
Reaction notes
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