Diethyl Ether → 2-Bromo-6-(tricyclo[3.3.1.13,7]dec-1-ylthio)benzonitrile

HRID 336597Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 336597
[C:1]12([SH:11])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[H-].[Na+].[Br:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:19](F)[C:16]=1[C:17]#[N:18].C(OCC)C>CS(C)=O>[C:1]12([S:11][C:19]3[CH:20]=[CH:21][CH:22]=[C:15]([Br:14])[C:16]=3[C:17]#[N:18])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 997301-AdamantylthiolHCID 27831392-Bromo-6-fluorobenzonitrile

Produkt 1

HCID 866812652-Bromo-6-(tricyclo[3.3.1.13,7]dec-1-ylthio)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

1-Adamantanethiol (278 mg) was dissolved in dimethyl sulfoxide (10 mL). Sodium hydride (60% in mineral oil, 42 mg) was added, and the solution was stirred at room temperature for 20 minutes. 2-Bromo-6-fluorobenzonitrile (300 mg) was added and the solution was heated to 130° C. for 1 hour. The solution was cooled, added to diethyl ether, washed with 1 M aqueous HCl three times, washed with brine, and dried over anhydrous sodium sulfate. After filtration, the solvent was removed under vacuum to yield the title compound.

Aufarbeitung

  1. temperaturethe solution was heated to 130° C. for 1 hour
  2. temperatureThe solution was cooled
  3. washwashed with 1 M aqueous HCl three times
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-13de4e6d8e0344ba87e154010480c2a1
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889675B2

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