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

HRID 245268ノート

反応式

HRID 245268 の反応式
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

参加物

5

反応物 3

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

生成物 1

HCID 146245254-Chloro-2,5-difluoroaniline収率 73.9%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-796432e67af04ee0b863b3d6e72bc1bb
出典データセット
uspto-grants-2014_02
特許番号
US08658791B2

反応ノート

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