乙酸乙酯 → 4-(二氟甲氧基)苯腈

HRID 3017

反应方程式

HRID 3017 反应方程式
[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

参与物

6

反应物 4

HCID 8857乙酸乙酯HCID 130194-羟基苯甲腈HCID 14798二甲基对苯二胺二盐酸HCID 2734985二氟氯乙酸钠

产物 1

HCID 27369904-(二氟甲氧基)苯腈收率 41%

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

实验过程

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.

后处理

  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.)

来源与证据

ORD记录
ord-9878f8a1a69f4990b1191065d489c660
来源数据集
uspto-grants-1998_03
专利号
US05731477

关联笔记

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