4-Nitrophenol → 4-(Difluoromethoxy)nitrobenzene

HRID 3018

反応式

HRID 3018 の反応式
[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

参加物

6

反応物 3

HCID 9804-NitrophenolHCID 14798Sodium HydroxideHCID 2734985Sodium chlorodifluoroacetate

生成物 1

HCID 27370144-(Difluoromethoxy)nitrobenzene収率 73.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
125 °C

実験手順

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.

後処理

  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 )

出典と根拠

ORDレコード
ord-b2d252a75b1947e3893ae5090ef4d0e4
出典データセット
uspto-grants-1998_03
特許番号
US05731477

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