Reaction #586152

Reaction equation

nitric acid

1-chloro-3-(2,6-dichloro-4-trifluoromethylphenyl)benzene

→

1-chloro-5-(2,6-dichloro-4-trifluoromethylphenyl)-2-nitrobenzene

Yield 52.6%

Solvents

Conditions

Workup

1. 1
   Extractionextracted with 100 ml of diethyl ether twice
2. 2
   WashThe diethyl ether layer was washed with 200 ml of water twice
3. 3
   Dryingdried over anhydrous magnesium sulfate
4. 4
   workup.DISTILLATIONthe diethyl ether was distilled off under reduced pressure
5. 5
   OtherPurification of the residue by silica gel column chromatography

Procedure

To 50 ml of fuming nitric acid, 5.0 g (15.4 mmol) of 1-chloro-3-(2,6-dichloro-4-trifluoromethylphenyl)benzene was added dropwise at −30° C. After 15 minutes of stirring at the same temperature, the reaction mixture was warmed to 5° C., poured into about 200 ml of ice-cold water and extracted with 100 ml of diethyl ether twice. The diethyl ether layer was washed with 200 ml of water twice and dried over anhydrous magnesium sulfate, and the diethyl ether was distilled off under reduced pressure. Purification of the residue by silica gel column chromatography afforded 3.0 g of 1-chloro-5-(2,6-dichloro-4-trifluoromethylphenyl)-2-nitrobenzene (yield 52.6%) as a pale yellow liquid (nD20 1.5744), which was used in Example 8 (2) as the starting material.

Source