Hydroxyamine hydrochloride → (NE)-N-[(4-bromo-2,5-difluorophenyl)methylidene]hydroxylamine

HRID 516548

Reaction equation

HRID 516548 reaction equation
[Br:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([CH:6]=O)=[C:4]([F:11])[CH:3]=1.Cl.[OH:13][NH2:14]>N1C=CC=CC=1.C(O)C.[Cl-].[NH4+]>[Br:1][C:2]1[C:9]([F:10])=[CH:8][C:5](/[CH:6]=[N:14]/[OH:13])=[C:4]([F:11])[CH:3]=1

Participants

6

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 224890814-Bromo-2,5-difluorobenzaldehyde

Product 1

HCID 90310471(NE)-N-[(4-bromo-2,5-difluorophenyl)methylidene]hydroxylamineYield 53.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1049PyridineSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A solution of 4-bromo-2,5-difluorobenzaldehyde (7.0 g, 31.67 mmol), hydroxyl amine hydrochloride (2.42 g, 34.84 mmol) in pyridine (35 mL) and ethanol (35 mL) was stirred at room temperature for 30 min. The reaction mixture was diluted with saturated ammonium chloride solution and extracted with ethyl acetate. The organic phase was washed with saturated brine solution, dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by flash chromatography (SiO2, eluting with 5-100% ethyl acetate in hexanes) to provide the title compound as a yellow solid (4.0 g, 53%): ESIMS m/z 238 [(M+2H)+].

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with saturated brine solution
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by flash chromatography (SiO2, eluting with 5-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2b742c3ec23b4560b2f4e16afbf75d16
Source dataset
uspto-grants-2015_08
Patent number
US09113629B2

Linked notes

Loading…