Azobisisobutyronitrile → 2-(Bromomethyl)-4-fluorobenzonitrile
Reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[CH:3]=1.C1C(=O)N([Br:18])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:10][C:4]1[CH:3]=[C:2]([F:1])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 4-fluoro-2-methylbenzonitrile (3) (2 g, 14.8 mmol), NBS (2.64 g, 15 mmol) and AIBN (100 mg) in CCl4 was refluxed under nitrogen for 2 hours. The reaction was cooled to room temperature. The solid was removed by filtration. The organic solution was concentrated to give crude product as an oil, which was used in the next step without further purification. 1H-NMR (400 MHz, CDCl3): δ 7.68 (dd, J=5.2, 8.4 Hz, 1H), 7.28 (dd, J=2.4, 8.8 Hz, 1H), 7.12 (m, 1H), 4.6 (s, 2H).
Workup
- temperaturewas refluxed under nitrogen for 2 hours
- customThe solid was removed by filtration
- concentrationThe organic solution was concentrated
- customto give crude product as an oil, which
- customwas used in the next step without further purification
Sources & evidence
- ORD record
- ord-9dbb4f524fc3408f9746bd83ad6daeaf
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093236B2
Reaction notes
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