Sodium hydride → 2-(3-Bromo-4-nitrophenyl)malonic acid tert-butyl ester methyl ester

HRID 494392

반응식

HRID 494392 반응식
[H-].[Na+].[C:3]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].[Br:15][C:16]1[CH:21]=[C:20](F)[CH:19]=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24]>CN(C)C=O>[CH3:8][O:7][C:5](=[O:6])[CH:4]([C:20]1[CH:19]=[CH:18][C:17]([N+:23]([O-:25])=[O:24])=[C:16]([Br:15])[CH:21]=1)[C:3]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 2733872tert-Butyl methyl malonateHCID 27569932-Bromo-4-fluoro-1-nitrobenzene

생성물 1

HCID 576832692-(3-Bromo-4-nitrophenyl)malonic acid tert-butyl ester methyl ester수율 163.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

반응 조건

온도
60 °C

실험 절차

Sodium hydride (60%, mineral oil; 0.985 g) was suspended in dimethylformamide (20 mL), and a solution of tert-butyl methyl malonate (4.29 g) in dimethylformamide (5 mL) was added dropwise thereto under ice-cooling. After foam generation is stopped, a solution of 2-bromo-4-fluoro-1-nitrobenzene (2.71 g) in dimethylformamide (5 mL) was added dropwise thereto at the same temperature, and the mixture was further stirred at 60° C. for 3 hours, and then concentrated. The residue was neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel with ethyl acetate:hexane=1:4 to 1:5 to give the title compound (7.54 g) as an oil.

후처리

  1. temperatureunder ice-cooling
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel with ethyl acetate

출처 및 근거

ORD 기록
ord-fd57106f1b3b45019f17b4dfbb54a26f
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538140B2

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