Acetate → 4-(Perfluoro3-iodopropyl)phenyl acetate

HRID 1112133ノート

反応式

HRID 1112133 の反応式
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8](I)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[I:12][C:13]([F:22])([F:21])[C:14]([F:20])([F:19])[C:15]([F:18])([F:17])I.IC(I)(C(F)(F)F)C(F)(F)F.C([O-])(=O)C>CS(C)=O.[Cu]>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:15]([F:18])([F:17])[C:14]([F:20])([F:19])[C:13]([F:22])([F:21])[I:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

参加物

7

反応物 4

HCID 175Acetate2 回HCID 1417934-IodophenylacetateHCID 109164621,1,2,2,3,3-Hexafluoro-1,3-diiodopropaneHCID 232361211,1,1,3,3,3-Hexafluoro-2,2-diiodopropane

生成物 1

HCID 213310104-(Perfluoro3-iodopropyl)phenyl acetate

試薬・触媒・溶媒 2

HCID 23978Copper触媒2 回HCID 679Dimethyl Sulfoxide溶媒

実験手順

The first stage of the process (equation A) involves reacting p-iodophenyl acetate (II) with 1,3-diiodohexafluoropropane (III). The reaction is conducted in anhydrous dimethyl sulfoxide (DMSO) in the presence of copper powder. Equimolar amounts of the reactants can be used, but it is usually preferred to employ an excess of the diiodohexafluoropropane e.g., 1 to 1.5 moles per mole of the acetate. For every mole of acetate, at least 2, e.g., about 2 to 10, gram atoms of copper are utilized. The reaction is carried out in an inert atmosphere at a temperature ranging from about 110° to 130° C. Examples of gases suitable for providing an inert atmosphere include nitrogen, helium and argon. The reaction period usually ranges from about 2 to 5 hours. At the end of the reaction period, the reaction product is recovered from the reaction mixture. In a preferred procedure, the reaction mixture is allowed to cool after which saturated aqueous ammonium chloride and methylene chloride are added. The excess copper and cuprous salts are then filtered off, and the organic layer is separated. After extracting the aqueous layer with additional methylene chloride, the organic extracts are combined, washed with water, dried over anhydrous magnesium sulfate, and finally reduced in volume to a light yellow oil. The oil is refluxed in acetic anhydride for about 30 minutes to one hour followed by removal of excess acetic anhydride and acetic acid by vacuum distillation. Distillation of the residual oil yields crude 4-(perfluoro-3-iodopropyl)phenyl acetate (IV) which is then purified by recrystallization from hexane.

後処理

  1. customranging from about 110° to 130° C
  2. customThe reaction period
  3. customAt the end of the reaction period
  4. customthe reaction product is recovered from the reaction mixture
  5. temperatureto cool after which saturated aqueous ammonium chloride and methylene chloride
  6. additionare added
  7. filtrationThe excess copper and cuprous salts are then filtered off
  8. customthe organic layer is separated
  9. extractionAfter extracting the aqueous layer with additional methylene chloride
  10. washwashed with water
  11. dry with materialdried over anhydrous magnesium sulfate
  12. temperatureThe oil is refluxed in acetic anhydride for about 30 minutes to one hour
  13. customfollowed by removal of excess acetic anhydride and acetic acid by vacuum distillation
  14. distillationDistillation of the residual oil

出典と根拠

ORDレコード
ord-04f1a89d813344b8b2a62d73f0ee7c0f
出典データセット
uspto-grants-1978_10
特許番号
US04120900

反応ノート

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