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

HRID 414267

反応式

HRID 414267 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3d5eb43172a14b90bf1cd55080bc599b
出典データセット
uspto-grants-1988_12
特許番号
US04791131

関連ノート

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