Ethanol → 2-(Difluoromethoxy)-6-methylaniline

HRID 1440720

반응식

HRID 1440720 반응식
C(O)C.[F:4][CH:5]([F:17])[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:8]=1[N+:14]([O-])=O.[Cl-].[Ca+2].[Cl-]>O.[Zn]>[F:4][CH:5]([F:17])[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:8]=1[NH2:14]

참가 물질

6

반응물 3

HCID 702EthanolHCID 5284359Calcium Chloride2회HCID 189816253-Difluoromethoxy-2-nitrotoluene

생성물 1

HCID 189816732-(Difluoromethoxy)-6-methylaniline수율 56.8%

시약·촉매·용매 2

HCID 23994Zinc촉매2회HCID 962Water용매3회

실험 절차

A mixture of 400 ml of absolute ethanol, 50 ml of water, 72.6 g of zinc dust, 53.3 g of the 2-(difluoromethoxy)-6-methylnitrobenzene, (Example 3A), and a solution of 20.0 g of calcium chloride dissolved in 60 ml of water was refluxed for three hours, allowed to stand overnight, refluxed for an additional hour, and then an additional 43 g of zinc dust and a solution of 18 g of calcium chloride dissolved in 50 ml of water was added. Refluxing for an additional three hours was required to drive the reaction to completion. The reaction was vacuum filtered through Celite®, the filter cake rinsed with 300 ml of ethanol and the filtrate concentrated to a volume of 100 ml. The liquid was diluted with 300 ml of ethyl acetate, 80 ml of 10% sodium hydroxide solution and 100 ml of water. A precipitate formed which was removed by vacuum filtration through Celite. The filter cake was rinsed with 200 ml of ethyl acetate. The phases were separated and the organic phase was dried with sodium sulfate, filtered and concentrated to yield 25.8 g of the desired intermediate as a black oil.

후처리

  1. temperaturewas refluxed for three hours
  2. temperaturerefluxed for an additional hour
  3. additionwas added
  4. temperatureRefluxing for an additional three hours
  5. customthe reaction to completion
  6. filtrationfiltered through Celite®
  7. washthe filter cake rinsed with 300 ml of ethanol
  8. concentrationthe filtrate concentrated to a volume of 100 ml
  9. additionThe liquid was diluted with 300 ml of ethyl acetate, 80 ml of 10% sodium hydroxide solution and 100 ml of water
  10. customA precipitate formed which
  11. customwas removed by vacuum filtration through Celite
  12. washThe filter cake was rinsed with 200 ml of ethyl acetate
  13. customThe phases were separated
  14. dry with materialthe organic phase was dried with sodium sulfate
  15. filtrationfiltered
  16. concentrationconcentrated

출처 및 근거

ORD 기록
ord-bfe359953c1546a38abebcfd9717e566
출처 데이터셋
uspto-grants-1996_03
특허 번호
US05500405

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