Water → 1-Bromo-3-cyclopropylthiobenzene

HRID 70580

Reaktionsgleichung

Reaktionsgleichung von HRID 70580
[CH3:1][C:2]([CH3:5])([O-])C.[K+].C1(Br)CC1.[Br:11][C:12]1[CH:13]=[C:14]([SH:18])[CH:15]=[CH:16][CH:17]=1.O>CS(C)=O>[Br:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([S:18][CH:5]2[CH2:2][CH2:1]2)[CH:13]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 78037BromocyclopropaneHCID 80597m-BromobenzenethiolHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 532169791-Bromo-3-cyclopropylthiobenzeneAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Potassium t-butoxide (4 g) and cyclopropyl bromide (7.6 mL) were added to a solution of 3-bromothiophenol (6 g) in dimethyl sulfoxide (30 mL), and the mixture was stirred at 80° C. for five hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was sequentially washed with water and brine, dried over sodium sulfate and filtered, after which the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→7:3) to give the title compound as a light yellow oil (1.6 g, 23%).

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was sequentially washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customafter which the solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→7:3)

Quellen und Nachweise

ORD-Eintrag
ord-a19d8c44d44b4ffb8dec7cb54f0906e5
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822503B2

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