Azobisisobutyronitrile → HCID 58443291, compound

HRID 1630747Notes

Reaction equation

HRID 1630747 reaction equation
[Cl:1][C:2]1[C:3]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[Br:16]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl.CCOC(C)=O>[Br:16][CH2:8][C:5]1[N:4]=[C:3]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)[C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 46311995HCID 46311995, compound

Product 1

HCID 58443291HCID 58443291, compound

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
74 °C

Procedure

To a solution of 3-chloro-2-(3-fluorophenyl)-6-methylpyridine (0.435 g, 2.0 mmol) in CCl4 (40 mL) was added N-bromosuccinimide (0.350 g, 2.0 mmol). The reaction mixture was heated to 74° C. and AIBN (0.027 g, 0.16 mmol) was added. The reaction mixture was heated to reflux for 1 d, diluted with EtOAc, washed with H2O (1×), brine (1×), dried over MgSO4, filtered through a pad of silica (1.5 cm), and concentrated. The product, 6-(bromomethyl)-3-chloro-2-(3-fluorophenyl)pyridine, was used without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 d
  3. washwashed with H2O (1×), brine (1×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered through a pad of silica (1.5 cm)
  6. concentrationconcentrated
  7. customThe product, 6-(bromomethyl)-3-chloro-2-(3-fluorophenyl)pyridine, was used without further purification

Sources & evidence

ORD record
ord-f322a4c4224c42eaad7f3dae3385465e
Source dataset
uspto-grants-2014_07
Patent number
US08791147B2

Reaction notes

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