Azobisisobutyronitrile → 2-Bromo-2-(4-bromo-2,6-difluorophenyl)acetamide
Reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH2:9][C:10]([NH2:12])=[O:11])=[C:4]([F:13])[CH:3]=1.[Br:14]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:14][CH:9]([C:5]1[C:4]([F:13])=[CH:3][C:2]([Br:1])=[CH:7][C:6]=1[F:8])[C:10]([NH2:12])=[O:11]Participants
5
Conditions
- Temperature
- 80 °C
Procedure
A solution of 2-(4-bromo-2,6-difluorophenyl)acetamide (0.4 g, 1.6 mmol) in carbon tetrachloride (5 mL) was degassed with nitrogen for 5 min. To this was added N-bromosuccinimide (0.28 g, 1.6 mmol) and then azobisisobutyronitrile (0.039 g, 0.24 mmol) while stirring. The reaction mixture was stirred at 80° C. overnight and then cooled to room temperature. The reaction mixture was concentrated to dryness in vacuo, and the residue was purified by flash chromatography (0-100% ethyl acetate/hexanes) to afford the title product (60 mg, 11%). MS(ES)+ m/e 328 [M+H]+.
Workup
- temperaturecooled to room temperature
- concentrationThe reaction mixture was concentrated to dryness in vacuo
- customthe residue was purified by flash chromatography (0-100% ethyl acetate/hexanes)
Sources & evidence
- ORD record
- ord-0bf44d77834740f7bc59322ff5fb0c3a
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09084794B2
Reaction notes
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