Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[Br:13]N1C(=O)CCC1=O>FC(C1C=CC=CC=1)(F)F.C(OCC)(=O)C.CC(N=NC(C#N)(C)C)(C#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:12][Br:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]Participants
6
Conditions
- Temperature
- 90 °C
Procedure
To a solution of methyl 5-bromo-2-methylbenzoate (5.27 g) in trifluoromethylbenzene (50.0 mL) were added AIBN (0.04 g) and N-bromosuccinimide (4.50 g), and the mixture was stirred at 90° C. for 4 hr under argon atmosphere. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (4.89 g).
Workup
- washthe mixture was washed with saturated brine
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-a7919ee28acd4adba6209dc2b2df2be1
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315458B2
Linked notes
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