Ethanol → Ethyl 4-bromo-2-fluorobenzoate
Reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([F:11])[CH:3]=1.S(Cl)(Cl)=O.C(=O)([O-])O.[Na+].[CH2:21](O)[CH3:22]>>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:21][CH3:22])=[O:7])=[C:4]([F:11])[CH:3]=1Participants
5
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 4-bromo-2-fluorobenzoic acid (3.0 g) in ethanol (20 mL) was added thionyl chloride (2.0 mL) at 0° C., and the mixture was stirred overnight at 70° C. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution, the mixture was concentrated under reduced pressure, and the residue was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (3.30 g).
Workup
- concentrationthe mixture was concentrated under reduced pressure
- extractionthe residue was extracted with ethyl acetate
- washThe organic layer was washed successively with water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-d2121bd063f9431c836e79c081a91b15
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09371320B2
Reaction notes
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