Sodium Chloride → 3-Bromo-1-{4-nitro-2-[(1E)-prop-1-en-1-yl]phenyl}pyridin-2(1H)-one

HRID 452234노트

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HRID 452234 반응식
[Br:1][C:2]1[C:3](=[O:8])[NH:4][CH:5]=[CH:6][CH:7]=1.CC(C)([O-])C.[K+].F[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:17]=1[CH:25]=[CH:26][CH3:27].[Cl-].[Na+]>CS(C)=O.O>[Br:1][C:2]1[C:3](=[O:8])[N:4]([C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:17]=2/[CH:25]=[CH:26]/[CH3:27])[CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 5234Sodium ChlorideHCID 8185493-Bromo-2-hydroxypyridineHCID 23665647Potassium tert-butoxideHCID 684983641-Fluoro-4-nitro-2-(prop-1-en-1-yl)benzene

생성물 1

HCID 595366023-Bromo-1-{4-nitro-2-[(1E)-prop-1-en-1-yl]phenyl}pyridin-2(1H)-one

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매2회HCID 962Water용매

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온도
0 °C

실험 절차

0.96 g (5.52 mmol) of 3-bromopyridin-2(1H)-one is dissolved in 17 ml of DMSO. The mixture is cooled to 0° C., and 1.00 g (5.52 mmol) of potassium tert-butoxide is added such that the internal temperature does not exceed 30° C. After 1 h at room temperature, a solution of 1.00 g (5.52 mmol) of the compound from Example 43A in 5 ml of DMSO is added. After 3 h at 80° C., 200 ml of water and 50 ml of sodium chloride solution are added and the mixture is extracted three times with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution and dried over sodium sulphate. The solvent is removed under reduced pressure and the product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate=4:1). This gives 935 mg (49% of theory) of the desired compound as an E/Z isomer mixture.

후처리

  1. customdoes not exceed 30° C
  2. waitAfter 3 h at 80° C.
  3. extractionthe mixture is extracted three times with ethyl acetate
  4. washThe combined organic phases are washed with saturated sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. customThe solvent is removed under reduced pressure
  7. customthe product is purified by chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate=4:1)

출처 및 근거

ORD 기록
ord-4dacd2c22d3542a9985385373661cac5
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487111B2

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