Stannous chloride dihydrate → 4-Chloro-2,5-difluoroaniline

HRID 245268노트

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HRID 245268 반응식
O.O.[Sn](Cl)Cl.[Cl:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([N+:14]([O-])=O)=[CH:9][C:8]=1[F:17].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[Cl:6][C:7]1[C:8]([F:17])=[CH:9][C:10]([NH2:14])=[C:11]([F:13])[CH:12]=1

참가 물질

5

반응물 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 157514831-Chloro-2,5-difluoro-4-nitrobenzene

생성물 1

HCID 146245254-Chloro-2,5-difluoroaniline수율 73.9%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
70 °C

실험 절차

Tin (II) chloride dihydrate (15.5 g, 68.7 mmol) was dissolved in ethyl acetate (50 mL) and 1-chloro-2,5-difluoro-4-nitrobenzene (2.65 g, 13.7 mmol) was added dropwise. The reaction mixture was then stirred at 70° C. for 1 h. The reaction mixture was then carefully added to saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The organic phase was washed several more times with water, dried, filtered, concentrated and purified by flash chromatography on silica gel (hexane/diethyl ether) to give the title compound as a white solid (1.65 g, 73.9% yield): 1H NMR (CDCl3) δ 7.02 (dd, 1H), 6.57 (dd, 1H), 3.81 (br s, 2H).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed several more times with water
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography on silica gel (hexane/diethyl ether)

출처 및 근거

ORD 기록
ord-796432e67af04ee0b863b3d6e72bc1bb
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658791B2

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