Azobisisobutyronitrile → HCID 57899326, compound

HRID 552918Notes

Reaction equation

HRID 552918 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[I:9].[Br:10]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>ClC1C=CC=CC=1>[Br:10][CH2:8][C:5]1[CH:6]=[N:7][C:2]([Cl:1])=[C:3]([I:9])[CH:4]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 299193742-Chloro-3-iodo-5-methylpyridine

Product 1

HCID 57899326HCID 57899326, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

4.60 g (18.15 mmol) of 6-chloro-5-iodo-3-methylpyridine (Setliff et al., J. Chem. Engineering Data (1976), 21(2), 246-7), 3.39 g (19.06 mmol) of N-bromosuccinimide and 0.30 g (1.82 mmol) of 2,2′-azobis(2-methylpropionitrile) in 500 ml of chlorobenzene are boiled under reflux for about 16 hours. The reaction mixture is washed with saturated aqueous sodium sulphite solution and sodium bicarbonate solution and then dried over sodium sulphate and concentrated under reduced pressure. Column cluomatography of the residue on silica gel (silica gel 60—Merck, particle size: 0.04 to 0.063 mm) using the mobile phase mixture ethyl acetate:cyclohexane (1:10) gives 3.86 g (38% of theory) of 3-bromomethyl-6-chloro-5-iodopyridine.

Workup

  1. temperatureunder reflux for about 16 hours
  2. washThe reaction mixture is washed with saturated aqueous sodium sulphite solution and sodium bicarbonate solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0eb9395a99f2467297ee680f9f389215
Source dataset
uspto-grants-2011_05
Patent number
US07951951B2

Reaction notes

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