4-Nitrophenol → 4-(Difluoromethoxy)nitrobenzene

HRID 3018

반응식

HRID 3018 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[C:12]([F:17])([F:16])C([O-])=O.[Na+].[OH-].[Na+]>CN(C=O)C.O>[F:16][CH:12]([F:17])[O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

참가 물질

6

반응물 3

HCID 9804-NitrophenolHCID 14798Sodium HydroxideHCID 2734985Sodium chlorodifluoroacetate

생성물 1

HCID 27370144-(Difluoromethoxy)nitrobenzene수율 73.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
125 °C

실험 절차

4-Nitrophenol (0.10 g, 0.72 mmol, Aldrich), sodium chlorodifluoroacetate (0.11 g, 0.72 mmol, Alfa Products) and sodium hydroxide (0.03 g, 0.72 mmol) were combined in dry DMF (1 mL) under an atmosphere of argon. After stirring at 125° C. for 1 h, the mixture was cooled to RT, was diluted with water and was extracted twice with ether. The combined organic extracts were washed twice with brine, were dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography (silica gel, 25% ethyl acetate/hexanes ) to provide the title compound as a white solid (0.10 g, 73%). mp 33°-35° C.

후처리

  1. temperaturethe mixture was cooled to RT
  2. extractionwas extracted twice with ether
  3. washThe combined organic extracts were washed twice with brine
  4. dry with materialwere dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash chromatography (silica gel, 25% ethyl acetate/hexanes )

출처 및 근거

ORD 기록
ord-b2d252a75b1947e3893ae5090ef4d0e4
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731477

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