Azobisisobutyronitrile → 2-(Bromomethyl)-4-fluorobenzonitrile

HRID 505907

Reaction equation

HRID 505907 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-70ffd7dc6f484aa1acea37b4f3ea4579
Source dataset
uspto-grants-2010_08
Patent number
US07781584B2

Linked notes

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