Water → 3-Cyano-4-(4-bromomethylphenyl)pyridine

HRID 373124Notes

Reaction equation

HRID 373124 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)#[N:2].[Br:16]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.O>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[C:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][Br:16])=[CH:11][CH:10]=1)#[N:2]

Participants

7

Reactant 4

HCID 962WaterHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 198115073-Cyano-4-(4-tolyl)pyridine

Product 1

HCID 183848873-Cyano-4-(4-bromomethylphenyl)pyridine

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-cyano-4-(4-tolyl)pyridine (485 mg, 2.66 mmol), N-bromosuccinimide (929 mg, 5.22 mmol), and dibenzoylperoxide (64 mg, 0.266 mmol) in CCl4 (15 mL) was heated to reflux for 6 h. The mixture was cooled and water (50 mL) and CH2Cl2 (30 mL) were added. The organic layer was dried (MgSO4) and purified by flash chromatography (10% EtOAc/hexanes). The product is not kept in concentrated form for more than 5 minutes and stored only in CH2Cl2 at 0° C. to minimize polymerization.

Workup

  1. temperatureto reflux for 6 h
  2. temperatureThe mixture was cooled
  3. dry with materialThe organic layer was dried (MgSO4)
  4. custompurified by flash chromatography (10% EtOAc/hexanes)
  5. waitThe product is not kept in concentrated form for more than 5 minutes
  6. customstored only in CH2Cl2 at 0° C.
  7. custompolymerization

Sources & evidence

ORD record
ord-a3e319e1b35045e7a8866e6939c3072d
Source dataset
uspto-grants-1992_11
Patent number
US05162325

Reaction notes

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