N-bromobutanimide → 1-(Bromomethyl)-2-fluoro-4-nitrobenzene
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[F:11].C1C(=O)N([Br:19])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[F:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 68 °C
Procedure
To a solution of 1-methyl-2-fluoro-4-nitrobenzene (4.96 g, 32 mmol) and NBS (6.05 g, 34 mmol) in CCl4 (80 mL) was added BPO (0.39 g, 1.6 mmol). The mixture was heated at 68° C. for 5 h, then filtered and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=20:1) to give the title compound as a yellow solid (4.53 g, 60%).
Workup
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=20:1)
Sources & evidence
- ORD record
- ord-4d8fba4631d94be49db7eb7c30cb4eea
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434695B2
Reaction notes
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