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

HRID 1503589Notes

Reaction equation

HRID 1503589 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-e616a06365774ced8648eef2ea2c24e1
Source dataset
uspto-grants-2015_12
Patent number
US09212163B2

Reaction notes

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