Azobisisobutyronitrile → 4'-(Bromomethyl)-2-cyanobiphenyl

HRID 1591469Notes

Reaction equation

HRID 1591469 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]#[N:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[Br:16]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:16][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:14]#[N:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 1455122-Cyano-4'-methylbiphenyl

Product 1

HCID 15019124'-(Bromomethyl)-2-cyanobiphenylYield 96.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 699 mg (3.62 mmol) of the intermediate obtained in Step B in 15 mL of carbon tetrachloride under nitrogen was added 708.3 mg (3.98 mmol, 1.1 eq) of N-bromosuccinimide and 59 mg (0.36 mmol, 0.1 eq) of azobisisobutyronitrile (AIBN). The resulting mixture was heated in the dark for 4 hours. The mixture was cooled to room temperature and filtered. The filtrate was concentrated under vacuum to afford 948 mg (96%) of the product as a yellow solid. 1H NMR (200 MHz, CDCl3): 4.51 (s,2H), 7.25-7.80 (m,8H). FAB-MS: calculated for C14H10BrN 272; found 272,274 (M+). 1H NMR indicates the presence of minor amounts of starting material and dibromo derivative.

Workup

  1. temperatureThe resulting mixture was heated in the dark for 4 hours
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-6ef5557aa2d34e51bceccb82cdbaca59
Source dataset
uspto-grants-1993_04
Patent number
US05206235

Reaction notes

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