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Hydrochloric Acid → 4-Fluorophenyldiphenylsulfonium difluoro-(2-hydroxyadamantan-2-yl)acetate

HRID 1506741
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1506741
[F:1][C:2]([F:19])([C:8]1([OH:18])[CH:15]2[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:17][CH:9]1[CH2:10]3)[CH2:14]2)[C:3]([O:5]CC)=[O:4].[OH-].[Na+].Cl.[Cl-].[F:24][C:25]1[CH:30]=[CH:29][C:28]([S+:31]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:27][CH:26]=1>C(Cl)Cl.O.O1CCOCC1>[F:1][C:2]([F:19])([C:8]1([OH:18])[CH:9]2[CH2:17][CH:13]3[CH2:12][CH:11]([CH2:16][CH:15]1[CH2:14]3)[CH2:10]2)[C:3]([O-:5])=[O:4].[F:24][C:25]1[CH:30]=[CH:29][C:28]([S+:31]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:27][CH:26]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 866496604-Fluorophenyldiphenylsulfonium chlorideHCID 117966647Ethyl difluoro-(2-hydroxy-adamantan-2-yl)acetate

Produkt 1

HCID 1317343634-Fluorophenyldiphenylsulfonium difluoro-(2-hydroxyadamantan-2-yl)acetateAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 2.6 g of ethyl difluoro-(2-hydroxyadamantan-2-yl)acetate, prepared in Synthesis Example 1-8, 30 g of 1,4-dioxane, 4.0 g of 25 wt % sodium hydroxide, and 10 g of water was stirred for 2 hours. To the reaction solution, 1.0 g of 35 wt % hydrochloric acid was added, and then 66 g of an aqueous solution of 4-fluorophenyldiphenylsulfonium chloride and 100 g of methylene chloride were added. After stirring for 30 minutes, the organic layer was taken out, washed with water, and concentrated under reduced pressure. Methyl isobutyl ketone was added to the concentrate, which was concentrated again. Diisopropyl ether was added to the concentrate. The supernatant was removed, leaving 2.4 g of the target compound, 4-fluorophenyldiphenylsulfonium difluoro-(2-hydroxyadamantan-2-yl)acetate as vitreous solids (yield 45%).

Aufarbeitung

  1. stirringAfter stirring for 30 minutes
  2. washwashed with water
  3. concentrationconcentrated under reduced pressure
  4. additionMethyl isobutyl ketone was added to the concentrate, which
  5. concentrationwas concentrated again
  6. additionDiisopropyl ether was added to the concentrate
  7. customThe supernatant was removed

Quellen und Nachweise

ORD-Eintrag
ord-fedf4ea1bb7143a6925d2c8584a3b5dd
Quelldatensatz
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09221742B2

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