N-bromobutanimide → 3-Bromo-2-methoxy-5-(trifluoromethyl)pyridine

HRID 1753206Notes

Reaction equation

HRID 1753206 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][N:4]=1.C1C(=O)N([Br:20])C(=O)C1>C(#N)C>[Br:20][C:8]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[C:6]([C:9]([F:12])([F:10])[F:11])[CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 27753122-Methoxy-5-(trifluoromethyl)pyridine

Product 1

HCID 148370183-Bromo-2-methoxy-5-(trifluoromethyl)pyridineYield 34.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 2-methoxy 5-(trifluoromethyl) pyridine (4 g, 22.58 mmol) was dissolved in acetonitrile (50 ml) was added NBS (6 g, 33.87 mmol) portion wise at 0° C. The reaction mixture was stirred for overnight at RT. The solvent was removed under vacuum, quenched with water (100 mL) and extracted with ethyl acetate. The combined organic layer was washed with water, brine, dried over sodium sulfate, and concentrated at reduced pressure to yield 3-bromo-2-methoxy-5-(trifluoromethyl)pyridine (12) as a pale yellow liquid (2 g, 34.7%).

Workup

  1. customThe solvent was removed under vacuum
  2. customquenched with water (100 mL)
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layer was washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-f8f8aec63b0142a99d32b4aa9a984ed3
Source dataset
uspto-grants-2015_10
Patent number
US09163020B2

Reaction notes

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