1-Propanol → 1-Iodo-2-methyl-4-propoxybenzene
Reaktionsgleichung
[CH2:1]([OH:4])[CH2:2][CH3:3].CC([O-])(C)C.[K+].F[C:12]1[CH:17]=[CH:16][C:15]([I:18])=[C:14]([CH3:19])[CH:13]=1>CN(C=O)C>[I:18][C:15]1[CH:16]=[CH:17][C:12]([O:4][CH2:1][CH2:2][CH3:3])=[CH:13][C:14]=1[CH3:19]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 80 °C
Versuchsvorschrift
3.44 mL (45.8 mmol) 1-propanol is added to an ice cold mixture of 3.42 g (30.5 mmol) KOtBu in 18 mL DMF. After stirring the mixture for 10 min 1.80 g (7.63 mmol) 4-fluoro-1-iodo-2-methylbenzene are added and the reaction mixture is stirred at 80° C. for 3 h. The reaction is quenched by the addition of a sat. aq. NH4Cl solution and extracted with EtOAc (2×). The combined organic layers are washed with sat. aq. NH4Cl solution and brine, dried with Na2SO4 and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel, heptane/EtOAc 9/1).
Aufarbeitung
- additionare added
- customThe reaction is quenched by the addition of a sat. aq. NH4Cl solution
- extractionextracted with EtOAc (2×)
- washThe combined organic layers are washed with sat. aq. NH4Cl solution and brine
- dry with materialdried with Na2SO4
- customthe solvent is removed in vacuo
- customThe crude product is purified by column chromatography (silica gel, heptane/EtOAc 9/1)
Quellen und Nachweise
- ORD-Eintrag
- ord-1fd5b82ef14e4689a84cf2f39b300bc9
- Quelldatensatz
- uspto-grants-2014_09
- Patentnummer
- US08835472B2
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