N-bromobutanimide → 4-(Bromomethyl)-3-fluorobenzonitrile

HRID 660265Notes

Reaction equation

HRID 660265 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH3:10])[C:5]#[N:6].[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:11][CH2:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 5851403-Fluoro-4-methylbenzonitrile

Product 1

HCID 27831494-(Bromomethyl)-3-fluorobenzonitrileYield 11.1%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 3-fluoro-4-methylbenzonitrile (5.0 g, 0.23 mol) in 100 mL of carbon tetrachloride was added N-bromosuccinimide (4.97 g, 0.28 mol) and AIBN (100 mg, 0.61 mmol) and the mixture was refluxed for six hours. The reaction was cooled and filtered. The filtrate was washed with water, dried over magnesium sulfate, filtered and the solvents were removed under vacuum to afford 5.44 g of the title compound as an off-white solid. 1H NMR indicated the presence of 20% starting material. 1H NMR (400 MHz, CDCl3) for the title compound: δ 7.54-7.30 (m, 3H), 4.83 (s, 2H).

Workup

  1. temperaturethe mixture was refluxed for six hours
  2. temperatureThe reaction was cooled
  3. filtrationfiltered
  4. washThe filtrate was washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvents were removed under vacuum

Sources & evidence

ORD record
ord-ef9d15e374ed4843a59b438d77c376bb
Source dataset
uspto-grants-2011_12
Patent number
US08084477B2

Reaction notes

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