Water → Methyl 2-(2-nitro-4-(trifluoromethyl)phenyl)acetate

HRID 388622ノート

反応式

HRID 388622 の反応式
[CH3:1][O:2][C:3](=[O:22])[CH:4]([C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:10]=1[N+:19]([O-:21])=[O:20])C(OC)=O.[Cl-].[Na+].O>CS(C)=O>[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:10]=1[N+:19]([O-:21])=[O:20]

参加物

5

反応物 3

HCID 962WaterHCID 5234Sodium ChlorideHCID 27635581,3-Dimethyl 2-[2-nitro-4-(trifluoromethyl)phenyl]propanedioate

生成物 1

HCID 83569Methyl 2-(2-nitro-4-(trifluoromethyl)phenyl)acetate

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
120 °C

実験手順

2-(2-Nitro-4-trifluoromethylphenyl)-malonic acid dimethyl ester (68 g, 0.21 mol) was dissolved in dimethyl sulfoxide (200 mL). Sodium chloride (34 g, 0.58 mol) and water (60 mL) were added and the mixture was stirred for 16-20 h at 120° C. (reaction monitored by TLC). The reaction mixture was then cooled to room temperature and quenched into water, which caused precipitation of the product. After stirring for 30 minutes, the product. (45 g, 80%) was isolated by filtration. The product was used without further purification in the next reaction. A small sample was crystallized (EtOAc/hexane, 2:8) for analysis, to yield yellow crystals, mp 104-105° C. 1H NMR (CDCl3) 8.3 (s, 1H), 7.88 (d, J=8.4 Hz, 1H), 7.50 (d, J=8.4 Hz, 1H), 4.12 (s, 2H), 3.60 (s, 3H). MS (FAB) m/z: 275.2 (M++1).

後処理

  1. custom(reaction monitored by TLC)
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. customquenched into water, which
  4. customprecipitation of the product
  5. stirringAfter stirring for 30 minutes
  6. custom(45 g, 80%) was isolated by filtration
  7. customThe product was used without further purification in the next reaction
  8. customA small sample was crystallized (EtOAc/hexane, 2:8) for analysis
  9. customto yield yellow crystals, mp 104-105° C

出典と根拠

ORDレコード
ord-980dbeea74934c869152bdc20e9429a5
出典データセット
uspto-grants-2013_02
特許番号
US08377958B2

反応ノート

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