Azobisisobutyronitrile → 6-(Bromomethyl)-3-methoxy-2-(4-(trifluoromethyl)phenyl)pyridine

HRID 1630745Notes

Reaction equation

HRID 1630745 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[N:5][C:6]([CH3:9])=[CH:7][CH:8]=1.C1C(=O)N([Br:27])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl.CCOC(C)=O>[Br:27][CH2:9][C:6]1[N:5]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[C:3]([O:2][CH3:1])=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 584432683-Methoxy-6-methyl-2-(4-(trifluoromethyl)phenyl)pyridine

Product 1

HCID 584433046-(Bromomethyl)-3-methoxy-2-(4-(trifluoromethyl)phenyl)pyridine

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-methoxy-6-methyl-2-(4-(trifluoromethyl)phenyl)pyridine (0.59 g, 2.2 mmol) in CCl4 (40 mL) was added NBS (440 mg, 2.5 mmol) and AIBN (33 mg, 0.20 mmol). The reaction mixture was heated to reflux for 13 h, diluted with EtOAc, washed with water (1×), brine (1×), dried over MgSO4, filtered through a pad (1.5 cm) of silica, and concentrated. The product 6-(bromomethyl)-3-methoxy-2-(4-(trifluoromethyl)phenyl)pyridine was used without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 13 h
  3. washwashed with water (1×), brine (1×)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered through a pad (1.5 cm) of silica
  6. concentrationconcentrated
  7. customThe product 6-(bromomethyl)-3-methoxy-2-(4-(trifluoromethyl)phenyl)pyridine was used without further purification

Sources & evidence

ORD record
ord-04e4e48fe9594a0cb0d5ec0154b8fee5
Source dataset
uspto-grants-2014_07
Patent number
US08791147B2

Reaction notes

Loading…