Isopropyl iodide → 1-Bromo-2-chloro-4-isopropoxybenzene

HRID 51023Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 51023
C([O-])([O-])=O.[K+].[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=1[Cl:15].I[CH:17]([CH3:19])[CH3:18]>CN(C=O)C>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH:17]([CH3:19])[CH3:18])=[CH:10][C:9]=1[Cl:15]

Komponenten

5

Edukt 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 70181824-Bromo-3-chlorophenol

Produkt 1

HCID 227354041-Bromo-2-chloro-4-isopropoxybenzeneAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A sample of K2CO3 (52.8 mmol, 7.4 g) was added to the 4-bromo-3-chloro-phenol (24 mmol, 5 g) in anhydrous DMF (100 mL) followed by the addition of 2-iodopropane (100 mmol, 10 mL). This stirred and heated at 60° C. overnight. The reaction was cooled, extracted into EtOAc (150 mL), washed with H2) (2 L), dried over MgSO4, and concentrated in vacuo, yielding 1-bromo-2-chloro-4-isopropoxybenzene as a brown oil (4.85 g, 81%). 1H NMR (CDCl3, 300 MHz): 7.35 (1H, d, J 8.7 Hz), 6.89 (1H, d, J 2.9 Hz), 6.57 (1H, dd, J 8.8 and 2.9 Hz), 4.38 (1H, m), 1.22 (6H, d, J 6.2 Hz.)

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. extractionextracted into EtOAc (150 mL)
  3. washwashed with H2) (2 L)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e3bc96d183c84e528eef0423ebf1c274
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713471B1

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