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

HRID 388622노트

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HRID 388622 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
120 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-980dbeea74934c869152bdc20e9429a5
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377958B2

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