Ethyl Acetate → 4-(Difluoromethoxy)benzonitrile

HRID 3017

반응식

HRID 3017 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].Cl[C:11]([F:16])([F:15])C([O-])=O.[Na+].[OH-].[Na+].C(OCC)(=O)C>CN(C=O)C>[F:15][CH:11]([F:16])[O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 130194-CyanophenolHCID 14798Sodium HydroxideHCID 2734985Sodium chlorodifluoroacetate

생성물 1

HCID 27369904-(Difluoromethoxy)benzonitrile수율 41%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-Cyanophenol (0.50 g, 4.2 mmol, Aldrich), sodium chlorodifluoroacetate (0.77 g, 5 mmol, Alfa Products), and sodium hydroxide (0.20 g, 5 mmol) were combined in dry DMF (2 mL) under an atmosphere of argon. After stirring at 125°-130° C. for 5 h, the mixture was cooled to RT, ethyl acetate (50 mL) was added and the organic layer was washed twice with brine. The organic extract was dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography (silica gel, 25% ethyl acetate/hexanes) to provide a white solid. The solid was sublimed (1 mm Hg, 23° C.) to provide the title compound as colorless crystals (0.29 g, 41%). mp 33°-35° C.

후처리

  1. washthe organic layer was washed twice with brine
  2. extractionThe organic extract
  3. dry with materialwas dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography (silica gel, 25% ethyl acetate/hexanes)
  7. customto provide a white solid
  8. custom(1 mm Hg, 23° C.)

출처 및 근거

ORD 기록
ord-9878f8a1a69f4990b1191065d489c660
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05731477

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