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

HRID 516548

반응식

HRID 516548 반응식
[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

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 702Ethanol용매HCID 1049Pyridine용매HCID 25517Ammonium Chloride용매

실험 절차

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)+].

후처리

  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)

출처 및 근거

ORD 기록
ord-2b742c3ec23b4560b2f4e16afbf75d16
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09113629B2

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