Azobisisobutyronitrile → 2-(Bromomethyl)-4-fluorobenzonitrile

HRID 1931247Notes

Reaction equation

HRID 1931247 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

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 38260554-Fluoro-2-methylbenzonitrile

Product 1

HCID 219849902-(Bromomethyl)-4-fluorobenzonitrile

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4-fluoro-2-methylbenzonitrile (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

  1. temperaturewas refluxed under nitrogen for 2 hours
  2. customThe solid was removed by filtration
  3. concentrationThe organic solution was concentrated
  4. customto give crude product as an oil, which
  5. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-bc059e8313444464a8c4cc6fbb139ee4
Source dataset
uspto-grants-2012_05
Patent number
US08188275B2

Reaction notes

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