Azobisisobutyronitrile → HCID 118272051, compound

HRID 590818Notes

Reaction equation

HRID 590818 reaction equation
[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[N:5]=[C:4]([Cl:11])[CH:3]=1.CC(N=NC(C#N)(C)C)(C#N)C.C1C(=O)N([Br:31])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:31][CH2:10][C:6]1[N:5]=[C:4]([Cl:11])[CH:3]=[C:2]([Cl:1])[C:7]=1[C:8]#[N:9]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 44597619HCID 44597619, compound

Product 1

HCID 118272051HCID 118272051, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 4,6-dichloro-2-methylnicotinonitrile (2.15 g, 11.50 mmol) in CCl4 (45 ml) was charged with AIBN (1.93 g, 11.75 mmol) and NBS (4.37 g, 24.55 mmol), sealed and heated to 75° C. for 16 hr. The mixture was poured directly onto SiO2 and purified via flash chromatography (5-15% Et2O/hexane) to provide 2-(bromomethyl)-4,6-dichloronicotinonitrile. MS ESI calc'd. for C7H4BrC12N2 [M+H]+ 265. found 265.

Workup

  1. customsealed
  2. additionThe mixture was poured directly onto SiO2
  3. custompurified via flash chromatography (5-15% Et2O/hexane)

Sources & evidence

ORD record
ord-e6b8888caa8b445a848a38d60b409dd3
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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