N-bromobutanimide → 5-Bromo-2-hydroxy-3-(trifluoromethyl)benzaldehyde
Reaction equation
[OH:1][C:2]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[Br:14]N1C(=O)CCC1=O>C(#N)C>[Br:14][C:7]1[CH:8]=[C:9]([C:10]([F:11])([F:12])[F:13])[C:2]([OH:1])=[C:3]([CH:6]=1)[CH:4]=[O:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2-hydroxy-3-trifluoromethylbenzaldehyde (59.16 g) was dissolved in acetonitrile (500 mL), and N-bromosuccinimide (57.56 g) was added to the solution, and then the mixture was stirred at 0° C. for 1 hour. The solvent was distilled off under reduced pressure and water was added, and then the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained crystal was washed with n-hexane (50 mL) to obtain the title compound (63.98 g) as a pale yellow crystal.
Workup
- distillationThe solvent was distilled off under reduced pressure and water
- additionwas added
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous sodium sulfate
- distillationThe solvent was distilled off under reduced pressure
- washthe obtained crystal was washed with n-hexane (50 mL)
Sources & evidence
- ORD record
- ord-df56cfcacc9c41299ed5df619c12927b
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367843B2
Reaction notes
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