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

HRID 414267

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HRID 414267 반응식
[H-].[Na+].[C:3]([O:10][CH3:11])(=[O:9])[CH2:4][C:5]([O:7][CH3:8])=[O:6].Br[C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=1[N+:20]([O-:22])=[O:21].[Cl-].[NH4+]>CS(C)=O>[Br:19][C:16]1[CH:17]=[CH:18][C:13]([CH:4]([C:3]([O:10][CH3:11])=[O:9])[C:5]([O:7][CH3:8])=[O:6])=[C:14]([N+:20]([O-:22])=[O:21])[CH:15]=1

참가 물질

6

반응물 4

HCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 770041,4-Dibromo-2-nitrobenzene

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
100 °C

실험 절차

To 9.4 g of sodium hydride was added 195 ml of dimethyl sulfoxide, followed by the dropwise addition of 22.37 ml of dimethyl malonate. At the end of the addition, the mixture was heated at 100° C. and maintained at that temperature for 40 minutes. At this point, 25 g of 1,4-dibromo-2-nitrobenzene was added all at once. The reaction mixture was maintained at 100° C. for 4 hours and then it was added to 1.0 liter of saturated ammonium chloride solution. The resulting mixture was extracted with ethyl acetate and the extracts were washed with ammonium chloride solution, water and saturated sodium chloride. The dried (MgSO4) solvent was evaporated, and the residue was recrystalized from ethyl acetate-hexane to give 22.45 g of dimethyl 2-(4-bromo-2-nitrophenyl)malonate.

후처리

  1. additionAt the end of the addition
  2. temperaturemaintained at that temperature for 40 minutes
  3. temperatureThe reaction mixture was maintained at 100° C. for 4 hours
  4. extractionThe resulting mixture was extracted with ethyl acetate
  5. washthe extracts were washed with ammonium chloride solution, water and saturated sodium chloride
  6. dry with materialThe dried (MgSO4) solvent
  7. customwas evaporated
  8. customthe residue was recrystalized from ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-3d5eb43172a14b90bf1cd55080bc599b
출처 데이터셋
uspto-grants-1988_12
특허 번호
US04791131

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