Ethyl Acetate → 4-(Difluoromethoxy)benzonitrile

HRID 3017

反応式

HRID 3017 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 27369904-(Difluoromethoxy)benzonitrile収率 41%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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.)

出典と根拠

ORDレコード
ord-9878f8a1a69f4990b1191065d489c660
出典データセット
uspto-grants-1998_03
特許番号
US05731477

関連ノート

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