Azobisisobutyronitrile → 4'-(Bromomethyl)-3'-fluorobiphenyl-2-carbonitrile

HRID 519901Notes

Reaction equation

HRID 519901 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]([C:15]#[N:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[Br:17]N1C(=O)CCC1=O.C1(C(F)(F)F)C=CC=CC=1.N(C(C)(C)C#N)=NC(C)(C)C#N>>[Br:17][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[C:10]([C:15]#[N:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 7368(Trifluoromethyl)benzeneHCID 67184N-bromobutanimideHCID 542386242-(3-Fluoro-4-methylphenyl)benzonitrile

Product 1

HCID 574600744'-(Bromomethyl)-3'-fluorobiphenyl-2-carbonitrile

Conditions

Temperature
78 °C

Procedure

To a mixture of 3′-fluoro-4′-methylbiphenyl-2-carbonitrile (110 g), N-bromosuccinimide (97.3 g) and benzotrifluoride (1.0 L) was added azobisisobutyronitrile (1.71 g), and the mixture was heated to an internal temperature of 78° C. and stirred for 16 hr. The reaction mixture was cooled to around 40° C., and the insoluble material was removed to give a solution of 4′-(bromomethyl)-3′-fluorobiphenyl-2-carbonitrile in benzotrifluoride.

Workup

  1. temperatureThe reaction mixture was cooled to around 40° C.
  2. customthe insoluble material was removed

Sources & evidence

ORD record
ord-514207afccb74fdfbc3112d1a64b872c
Source dataset
uspto-grants-2015_08
Patent number
US09115136B2

Reaction notes

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