Reaktion #55594

Reaktionsgleichung

m-Chlorofluorobenzene

sulfuric acid

nitric acid

benzene

→

3-chloro-4-nitrofluorobenzene

Ausbeute 16.7%

Lösungsmittel

hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe extract is washed with water (1×300 ml.), sodium carbonate solution (1×300 ml.), and water (1×300 ml.)
2. 2
   Sonstigedried
3. 3
   Sonstigethe solvents removed
4. 4
   workup.DISTILLATIONThe residue is distilled
5. 5
   Sonstigeto give 138 g
6. 6
   SonstigeThe 4-nitro isomer crystallizes
7. 7
   Filtrationis filtered off

Vorschrift

m-Chlorofluorobenzene (240 g. 1.85 moles) is added to a mixture of sulfuric acid (185 g. 1.85 moles) and nitric acid (166 g., 1.85 moles) at -5° C. in 3.5 hours, stirred 13 hours, then benzene (200 ml.) and hexane (200 ml.) are added. The extract is washed with water (1×300 ml.), sodium carbonate solution (1×300 ml.), and water (1×300 ml.), dried and the solvents removed. The residue is distilled to give 138 g. of mixed isomers. The 4-nitro isomer crystallizes and is filtered off to give 3-chloro-4-nitrofluorobenzene (51 g. 16.7%) m.p. 36°-38° C.

Quelle