Benzoyl Peroxide → 2-Cyano-3-(4-bromomethylphenyl)pyridine

HRID 373128Notes

Reaction equation

HRID 373128 reaction equation
[C:1]([C:3]1[C:8]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].[Br:16]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:1]([C:3]1[C:8]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][Br:16])=[CH:11][CH:10]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 153301703-(4-Methylphenyl)pyridine-2-carbonitrile

Product 1

HCID 183845142-Cyano-3-(4-bromomethylphenyl)pyridine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-cyano-3-(4-tolyl)pyridine (940 mg, 4.84 mmol), N-bromosuccinimide (1.03 mg, 5.81 mmol), and dibenzoylperoxide (117 mg, 0.48 mmol) in CCl4 (70 mL) was heated to reflux to 2 h. The mixture was cooled then filtered through 50 g of silica gel eluting with CH2Cl2. The product was purified further by flash chromatography (20% EtOAc/hexanes) to give the above titled compound as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux to 2 h
  3. temperatureThe mixture was cooled
  4. filtrationthen filtered through 50 g of silica gel eluting with CH2Cl2
  5. customThe product was purified further by flash chromatography (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2b135ccea06840ce8da8b6980c5a27f3
Source dataset
uspto-grants-1992_11
Patent number
US05162325

Reaction notes

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