Azobisisobutyronitrile → 4-Cyano-3-fluorobenzyl bromide

HRID 425968Notes

Reaction equation

HRID 425968 reaction equation
[Br:1]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C.[F:21][C:22]1[CH:29]=[C:28]([CH3:30])[CH:27]=[CH:26][C:23]=1[C:24]#[N:25]>C(Cl)(Cl)(Cl)Cl>[Br:1][CH2:30][C:28]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[C:22]([F:21])[CH:29]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 27784432-Fluoro-4-methylbenzonitrile

Product 1

HCID 27784664-Cyano-3-fluorobenzyl bromide

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Bromosuccinimide and AIBN were added to a carbon tetrachloride solution of 2-fluoro-4-methylbenzonitrile, followed by heating under reflux to obtain 4-(bromomethyl)-2-fluorobenzonitrile. By allowing this to react with morpholine in DMF in the presence of potassium carbonate, 2-fluoro-4-(morpholin-4-ylmethyl)benzonitrile was obtained. In DMF and in the presence of potassium carbonate, this was allowed to react with cyclohexanamine at 160° C. for 30 minutes while carrying out microwave irradiation. By post-treating the reaction liquid, 2-(cyclohexylamino)-4-(morpholin-4-ylmethyl)benzonitrile was obtained.

Workup

  1. temperatureby heating
  2. temperatureunder reflux

Sources & evidence

ORD record
ord-31a9af376a1240b4b8f70bdeb7fc91cd
Source dataset
uspto-grants-2012_01
Patent number
US08106190B2

Reaction notes

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