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

HRID 494392

反応式

HRID 494392 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fd57106f1b3b45019f17b4dfbb54a26f
出典データセット
uspto-grants-2009_05
特許番号
US07538140B2

関連ノート

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