(1-Bromo-2,2-dimethylpropyl)benzene → HCID 87316481, Verbindung

HRID 1844379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1844379
Br[CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([CH3:6])([CH3:5])[CH3:4].[C:13]([O-:16])(=[S:15])[CH3:14].[K+]>CN(C=O)C>[CH3:4][C:3]([CH3:6])([CH3:5])[CH:2]([S:15][C:13](=[O:16])[CH3:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

4

Edukt 2

HCID 14912426(1-Bromo-2,2-dimethylpropyl)benzeneHCID 23670855Potassium ethanethioate

Produkt 1

HCID 87316481HCID 87316481, VerbindungAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

(1-Bromo-2,2-dimethyl-propyl)-benzene (1.00 g, 4.40 mmol) was dissolved in dry DMF (5 mL) under an argon atmosphere. Potassium thioacetate (2.51 g, 22.0 mmol) was added and the reaction was heated to 50° C. for 7 days. The solution was then concentrated and the product purified by column chromatography to obtain the desired thioester (970 mg, 99%). TLC (Hexane:CH2Cl2, 7:3 v/v): Rf=0.40. 1H NMR (400 MHz, CDCl3): δ 7.33-7.22 (m, 5H), 4.52 (s, 1H), 2.32 (s, 3H), 1.00 (s, 9H). 13C NMR (100 MHz, CDCl3): δ 193.9 (q), 140.4 (q), 129.0, 127.2, 126.4, 58.7, 34.9 (q), 30.2, 27.6. HRMS (m/z): [M+Na]+ calcd. for C13H18ONaS 245.0976; found, 245.0972.

Aufarbeitung

  1. concentrationThe solution was then concentrated
  2. customthe product purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-75eafea52e424fd195bda8cfc61eaa40
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946429B2

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