4-Nitrophenol → 4-(Difluoromethoxy)nitrobenzene

HRID 3020

반응식

HRID 3020 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:18])([F:17])C(OC)=O.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[F:17][CH:12]([F:18])[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 4

HCID 9804-NitrophenolHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 73935Methyl chlorodifluoroacetate

생성물 1

HCID 27370144-(Difluoromethoxy)nitrobenzene수율 65%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-Nitrophenol (0.14 g, 1.0 mmol, Aldrich), methyl chlorodifluoroacetate (0.29 g, 2.0 mmol, Aldrich) and potassium carbonate (0.29 g, 2.1 mmol) were combined in dry DMF (0.5 mL) under an argon atmosphere. After stirring at 95°-100° C. for 0.5 h, the mixture was cooled to RT, ethyl acetate (20 mL) was added and the organic layer was washed three times with 10% NaOH. The organic extract was dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography (silica gel, 20% ether/hexanes) to provide the title compound as a white solid (0.12 g, 65%). mp 33°-35° C.

후처리

  1. washthe organic layer was washed three times with 10% NaOH
  2. extractionThe organic extract
  3. dry with materialwas dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography (silica gel, 20% ether/hexanes)

출처 및 근거

ORD 기록
ord-78322038f273421dabe49798105b950a
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731477

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