m-Fluorotoluene → 5-Fluoro-2-nitrotoluene

Participants

Reaction Steps

3-Fluorotoluene (1 mole) in concentrated sulfuric acid (200 ml.) is stirred at 0° C. while a cold solution of potassium nitrate (1.5 mole) in concentrated sulfuric acid (750 ml.) is added slowly during 3 hours, the temperature being kept below 5° C. with an ice-ethanol bath After the addition is complete, the ice-bath is removed and stirring is continued for 3 hours at room temperature. Water (400 ml.) is added, and the organic layer is separated, dried (MgSO4) and filtered. The oil is separated by vapor-phase chromatograph on a 200×1 cm. silicone oil column (DC 200 20%) on Chromosorb R (60/80) at 191° C. and a helium flow rate of 86 ml./min. The desired pure nitro-isomer is collected.

Provenance & Evidence