Azobisisobutyronitrile → 5-(Bromomethyl)-2-fluorobenzonitrile

HRID 1357735Notes

Reaction equation

HRID 1357735 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH3:10])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].[Br:11]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C1C=CC=CC=1>[C:1]([C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[F:9])[CH2:10][Br:11])#[N:2]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 27745842-Fluoro-5-methylbenzonitrile

Product 1

HCID 27739315-(Bromomethyl)-2-fluorobenzonitrileYield 63.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 3-Cyano-4-fluorotoluene (1.0 g, 7.4 mmol), N-bromosuccinimide (1.3 g, 7.4 mmol) and catalytic 2,2′-azobisisobutyronitrile (AIBN) in benzene was heated to reflux for 16 hours, evaporated to dryness and flash chromatographed over silica gel eluting with 10% ethyl acetate/hexane to provide 1.0 g of 3-cyano-4-fluorobenzyl bromide.

Workup

  1. temperatureto reflux for 16 hours
  2. customevaporated to dryness and flash
  3. customchromatographed over silica gel eluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-37a406487160451ab76c17ba3973af62
Source dataset
uspto-grants-2003_07
Patent number
US06593335B1

Reaction notes

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