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

HRID 422032

反応式

HRID 422032 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:12][C:13]1[CH:18]=[CH:17][C:16](F)=[C:15]([N+:20]([O-:22])=[O:21])[CH:14]=1>CS(C)=O>[CH3:8][O:7][C:5](=[O:6])[CH:4]([C:16]1[CH:17]=[CH:18][C:13]([Br:12])=[CH:14][C:15]=1[N+:20]([O-:22])=[O:21])[C:3]([O:10][CH3:11])=[O:9]

参加物

5

反応物 3

HCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 27363284-Bromo-1-fluoro-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
60 °C

実験手順

To a suspension of NaH (60% in mineral oil, 972 mg, 24.3 mmol) in DMSO (16 mL) is added dimethyl malonate (2.78 mL, 24.3 mmol). The mixture is heated at 60° C. for 10 min and then is cooled to room temperature before 4-bromo-1-fluoro-2-nitro-benzene (1.0 mL, 8.1 mmol) is added. The resulting mixture is heated at 60° C. for 3 hr and then is quenched with saturated aqueous NH4Cl solution. The mixture is extracted with EtOAc, washed with brine, dried over MgSO4, and concentrated. The crude is used without further purification.

後処理

  1. additionis added
  2. temperatureThe resulting mixture is heated at 60° C. for 3 hr
  3. customis quenched with saturated aqueous NH4Cl solution
  4. extractionThe mixture is extracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe crude is used without further purification

出典と根拠

ORDレコード
ord-c24f09dbbd18411d807358b383b3f8db
出典データセット
uspto-grants-2012_01
特許番号
US08101608B2

関連ノート

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