(NE)-N-[(5-bromo-2-fluoro-3-methylphenyl)methylidene]hydroxylamine → 5-Bromo-2-fluoro-3-methyl-benzonitrile

HRID 1502758Notes

Reaction equation

HRID 1502758 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

HCID 89306402(NE)-N-[(5-bromo-2-fluoro-3-methylphenyl)methylidene]hydroxylamine

Product 1

HCID 711383595-Bromo-2-fluoro-3-methyl-benzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7918Acetic AnhydrideSolvent

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

  1. temperatureto reflux for 18 h
  2. extractionextracted with ethyl acetate
  3. washThe combined ethyl acetate layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c0b6d87f9e944b5cb3ed4a449a76832e
Source dataset
uspto-grants-2015_12
Patent number
US09210927B2

Reaction notes

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