(NE)-N-[(5-bromo-2-fluoro-3-methylphenyl)methylidene]hydroxylamine → 5-Bromo-2-fluoro-3-methyl-benzonitrile
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([F:11])=[C:6]([CH:10]=1)/[CH:7]=[N:8]/O>C(OC(=O)C)(=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([F:11])=[C:6]([CH:10]=1)[C:7]#[N:8]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A stirred solution of (E)-5-bromo-2-fluoro-3-methylbenzaldehyde oxime (0.5 g, 2.2 mmol) in acetic anhydride (5.0 mL) was heated to reflux for 18 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined ethyl acetate layer was washed with brine and dried over Na2SO4 and concentrated under reduced pressure to afford the crude compound as a light brown gummy material (0.4 g, crude): ESIMS m/z 213.82 ([M+H]+).
Workup
- temperatureto reflux for 18 h
- extractionextracted with ethyl acetate
- washThe combined ethyl acetate layer was washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-0dad634e28ec4fc99b78418f8d552259
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09211280B2
Reaction notes
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