Azobisisobutyronitrile → Methyl 4-(bromomethyl)-3-iodobenzoate
Reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].C1C(=O)N([Br:20])C(=O)C1.N(C(C)(C)C#N)=NC(C)(C)C#N.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[I:1]Participants
6
Conditions
- Temperature
- 70 °C
Procedure
Into a 100-mL round-bottom flask, was placed a mixture of methyl 3-iodo-4-methylbenzoate (compound 5.3, 3.00 g, 10.9 mmol) in CCl4 (50 mL), NBS (2.9 g, 16.3 mmol), azobisisobutyronitrile (360 mg, 2.19 mmol) and potassium carbonate (1.65 g, 11.9 mmol). The resulting mixture was stirred overnight at 70° C., then cooled to room temperature and concentrated under reduced pressure. The residue was diluted with EtOAc (100 mL) and the mixture was washed with brine (2×50 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:20) as the eluent to yield 3.0 g (78%) of the title compound as a yellow solid.
Workup
- customInto a 100-mL round-bottom flask, was placed
- temperaturecooled to room temperature
- concentrationconcentrated under reduced pressure
- additionThe residue was diluted with EtOAc (100 mL)
- washthe mixture was washed with brine (2×50 mL)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:20) as the eluent
Sources & evidence
- ORD record
- ord-4b1c588599a942a2ba37b6f927d1b774
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428502B2
Reaction notes
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