Isopropanol → 1-Chloro-5-isopropoxy-2-methyl-4-nitrobenzene

HRID 386763

Reaktionsgleichung

Reaktionsgleichung von HRID 386763
[Cl:1][C:2]1[CH:7]=[C:6](F)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH3:12].C([O-])([O-])=O.[Cs+].[Cs+].[CH3:19][CH:20]([OH:22])[CH3:21]>>[Cl:1][C:2]1[CH:7]=[C:6]([O:22][CH:20]([CH3:21])[CH3:19])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[CH3:12]

Komponenten

4

Edukt 3

HCID 3776Isopropanol2×HCID 10796Cesium carbonateHCID 101039792-Chloro-4-fluoro-5-nitrotoluene

Produkt 1

HCID 457903241-Chloro-5-isopropoxy-2-methyl-4-nitrobenzene

Versuchsvorschrift

To a solution of 25 g (0.131 mol) of 2-chloro-4-fluoro-5-nitrotoluene in 250 ml of 2-propanol is added 208 g (0.659 mol, 5 eq.) of Cs2CO3. The mixture is stirred at 60° C. overnight and most of the 2-propanol is evaporated under reduced pressure. Water is added and the solution is extracted with EtOAc. The organic layers are combined, dried over MgSO4, concentrated and the crude product filtrated over a silica plug (eluent: 95/5 hexanes/EtOAc) to afford 2-chloro-4-isopropoxy-5-nitrotoluene as a pale yellow fluffy solid.

Aufarbeitung

  1. customis evaporated under reduced pressure
  2. additionWater is added
  3. extractionthe solution is extracted with EtOAc
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. filtrationthe crude product filtrated over a silica plug (eluent: 95/5 hexanes/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-56e878de7c8542ada3a8ea15f4ee33b9
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372858B2

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