Azobisisobutyronitrile → 2-(Bromomethyl)-4-fluorobenzonitrile

HRID 2193432Notes

Reaction equation

HRID 2193432 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-91d968d3b7874ccaab111c8ced345caa
Source dataset
uspto-grants-2012_12
Patent number
US08329900B2

Reaction notes

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