Azobisisobutyronitrile → 4-Bromomethyl-2-fluoropyridine

HRID 1955165Notes

Reaction equation

HRID 1955165 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[Br:9]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)Cl>[Br:9][CH2:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 27374032-Fluoro-4-methylpyridine

Product 1

HCID 139851684-Bromomethyl-2-fluoropyridineYield 21.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2-fluoro-4-methylpyridine (0.5 g) in chloroform (50 ml) was treated with N-bromosuccinimide (1.35 g) and azobisisobutyronitrile (0.25 g). The mixture was heated at reflux for 30 hours, cooled to room temperature and washed with water (30 ml). The chloroform solution was evaporated and the resulting brown oil purified by flash chromatography on silica eluting initially with a mixture of ethyl acetate and pentane (1:9, v/v) then with a mixture of ethyl acetate and pentane (15:85, v/v). Fractions homogenous in the required product were combined and evaporated affording the title compound (0.18 g) as a yellow oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 30 hours
  3. washwashed with water (30 ml)
  4. customThe chloroform solution was evaporated
  5. customthe resulting brown oil purified by flash chromatography on silica eluting initially with a mixture of ethyl acetate and pentane (1:9, v/v)
  6. additionwith a mixture of ethyl acetate and pentane (15:85
  7. customevaporated

Sources & evidence

ORD record
ord-c75e85571bad447b8dec596b9c17cadc
Source dataset
uspto-grants-2000_09
Patent number
US06124343

Reaction notes

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