Dimethyl malonate → 1,3-Dimethyl 2-(4-bromo-2-nitrophenyl)propanedioate

HRID 428283

반응식

HRID 428283 반응식
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].[Br:12][C:13]1[CH:14]=[CH:15][C:16](F)=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=1>CS(C)=O>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([CH:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])=[C:17]([N+:19]([O-:21])=[O:20])[CH:18]=1

참가 물질

5

반응물 3

HCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

생성물 1

HCID 157405961,3-Dimethyl 2-(4-bromo-2-nitrophenyl)propanedioate

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

반응 조건

온도
100 °C

실험 절차

Dimethyl malonate (13 mL) was added dropwise to 2.7 g sodium hydride suspended in 20 mL dimethylsulfoxide. The mixture was heated to 100° C. for 10 minutes and then cooled to room temperature. 5-Bromo-2-fluoronitrobenzene (5.0 g) in 25 mL of dimethylsulfoxide was added and the mixture was heated at 100° C. for 2 hours. The reaction mixture was cooled and quenched with 300 mL of saturated ammonium chloride solution and extracted three times with ethyl acetate. The extracts were combined, washed with saturated ammonium chloride, water and brine, dried over anhydrous sodium sulfate and concentrated to give crude dimethyl 4-bromo-2-nitrophenylmalonate as a pale yellow oil.

후처리

  1. temperaturecooled to room temperature
  2. temperaturethe mixture was heated at 100° C. for 2 hours
  3. temperatureThe reaction mixture was cooled
  4. customquenched with 300 mL of saturated ammonium chloride solution
  5. extractionextracted three times with ethyl acetate
  6. washwashed with saturated ammonium chloride, water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-03d6d163236f49ce8eace9b37837f7b1
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313158B1

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