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Hydrochloric Acid → ethyl 6-nonafluorobutyl-2,2-bis(fluoromethyl)-2H-1-benzopyran-4-carboxylate

HRID 264863
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 264863
[F:1][CH2:2][C:3]1([CH2:19][F:20])[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:6]2[CH:14]=[C:15](I)[CH:16]=[CH:17][C:5]=2[O:4]1.[F:21][C:22]([F:34])([C:30]([F:33])([F:32])[F:31])[C:23]([F:29])([F:28])[C:24](I)([F:26])[F:25].CN(C)P(=O)(N(C)C)N(C)C.Cl>[Cu].C(OCC)(=O)C>[F:21][C:22]([F:34])([C:30]([F:31])([F:32])[F:33])[C:23]([F:28])([F:29])[C:24]([F:25])([F:26])[C:15]1[CH:16]=[CH:17][C:5]2[O:4][C:3]([CH2:19][F:20])([CH2:2][F:1])[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:6]=2[CH:14]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 12679HexamethylphosphoramideHCID 67917Perfluorobutyl iodide2×HCID 19037016ethyl 2,2-bisfluoromethyl-6-iodo-2H-1-benzopyran-4-carboxylate

Produkt 1

HCID 19037030ethyl 6-nonafluorobutyl-2,2-bis(fluoromethyl)-2H-1-benzopyran-4-carboxylateAusbeute 51,3 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 23978CopperKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 0.30 g of ethyl 2,2-bis(fluoromethyl)-6-iodo-2H-1-benzopyran-4-carboxylate, 3.50 g of nonafluoro-butyl iodide, 0.30 g of copper powder, 0.32 g of cuprous iodide and 3 ml of hexamethylphosphoric triamide was stirred with heating at 70° C. for 22 hours, added another 1.75 g of nonafluorobutyl iodide, and stirred with heating at 150° C. for 5 hours. A mixture of 2N HCl and ethyl acetate was added to the reaction mixture, and insoluble materials were separated off using a celite. An organic layer was taken up, and an aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with saturated sodium chloride solution, dried over sodium sulfate, and concentrated in vacuo. The resultant residue was purified with silica gel column chromatography (developing solution, methylene chloride:hexane=5:1) to obtain 0.19 g of ethyl 6-nonafluorobutyl-2,2-bis(fluoromethyl)-2H-1-benzopyran-4-carboxylate as an oil.

Aufarbeitung

  1. stirringstirred
  2. temperaturewith heating at 150° C. for 5 hours
  3. additionwas added to the reaction mixture, and insoluble materials
  4. customwere separated off
  5. extractionan aqueous layer was extracted with ethyl acetate
  6. washwashed with saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe resultant residue was purified with silica gel column chromatography (developing solution, methylene chloride:hexane=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-e2d450789e04499281cfc8bf3b4811bb
Quelldatensatz
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05646308

Notizen zur Reaktion

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