Hydrochloric Acid → (2Z)-1-(4-bromophenyl)-2-hydroxyiminopentan-1-one

HRID 1873912노트

반응식

HRID 1873912 반응식
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:14])[CH2:10][CH2:11][CH2:12][CH3:13])=[CH:5][CH:4]=1.[N:15]([O-])=[O:16].[Na+]>C1COCC1.C(OCC)C>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([C:9](=[O:14])/[C:10](=[N:15]\[OH:16])/[CH2:11][CH2:12][CH3:13])=[CH:7][CH:8]=1

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 817174'-BromovalerophenoneHCID 23668193Sodium Nitrite

생성물 1

HCID 87519930(2Z)-1-(4-bromophenyl)-2-hydroxyiminopentan-1-one수율 59.1%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

The conc. HCl (40 mL) was added dropwise to a solution of 1-(4-bromophenyl)pentan-1-one (4.68 g, 19.41 mmol) and sodium nitrite (4.02 g, 58.2 mmol) in THF (80 ml) at 0° C. and allowed to warm to room temperature and stirred 18 hours. The reaction mixture was diluted with diethyl ether and the organic phase washed with sat'd NaHCO3 and brine. Concentration gave (Z)-1-(4-bromophenyl)-2-(hydroxyimino)pentan-1-one 3.1 g (33%) as an oil which was used without further purification.). RT=2.1 min, (Condition 1) LCMS: Anal. Calcd. for C11H12BrN1O2 270.01. found: 270.15 (M+H)+.

후처리

  1. washthe organic phase washed with sat'd NaHCO3 and brine
  2. concentrationConcentration

출처 및 근거

ORD 기록
ord-4901a9bc8e0e45128a7b2683e10d12e2
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08303944B2

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