N-bromobutanimide → 2-Bromo-1-[6-(difluoromethoxy)pyridin-3-yl]ethan-1-one

HRID 633769노트

반응식

HRID 633769 반응식
C([O:5][C:6]([C:8]1[CH:9]=[CH:10][C:11]([O:14][CH:15]([F:17])[F:16])=[N:12][CH:13]=1)=[CH2:7])CCC.[Br:18]N1C(=O)CCC1=O>C1COCC1.O.O>[Br:18][CH2:5][C:6]([C:8]1[CH:13]=[N:12][C:11]([O:14][CH:15]([F:17])[F:16])=[CH:10][CH:9]=1)=[O:7]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 118199865HCID 118199865, 화합물

생성물 1

HCID 1181998662-Bromo-1-[6-(difluoromethoxy)pyridin-3-yl]ethan-1-one수율 75.2%

시약·촉매·용매 2

HCID 962Water용매HCID 21881883Oxolane--water (1/1)용매

반응 조건

온도
0 °C

실험 절차

A solution of 100 mg (0.41 mmol) of 5-(1-butoxyvinyl)-2-difluoromethoxypyridine in 4 mL of THF/H2O (3/1: v/v) is cooled to 0° C. 74 mg (0.41 mmol) of N-bromosuccinimide are then added in a single portion. The yellow solution is stirred at 0° C. for 1 hour and then taken up in water and extracted with EtOAc. The organic phase is washed with saturated aqueous NaHCO3 solution and then with saturated NaCl solution, dried over magnesium sulfate and then evaporated to dryness. The crude product is purified by chromatography on silica gel (eluent: 20/80 EtOAc/heptane to 40/60 EtOAc/heptane over 15 minutes) to give 82 mg of 2-bromo-1-(6-difluoromethoxypyrid-3-yl)ethanone, corresponding to the following characteristics:

후처리

  1. extractionextracted with EtOAc
  2. washThe organic phase is washed with saturated aqueous NaHCO3 solution
  3. dry with materialwith saturated NaCl solution, dried over magnesium sulfate
  4. customevaporated to dryness
  5. customThe crude product is purified by chromatography on silica gel (eluent: 20/80 EtOAc/heptane to 40/60 EtOAc/heptane over 15 minutes)

출처 및 근거

ORD 기록
ord-f36da45fcf604d4fb0169556ec4d7c5b
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321790B2

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