Nitric Acid → 1-Chloro-5-(2,6-dichloro-4-trifluoromethylphenyl)-2-nitrobenzene

HRID 25307Notes

Reaction equation

HRID 25307 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([C:19]([F:22])([F:21])[F:20])=[CH:14][C:13]=2[Cl:23])[CH:7]=1>>[Cl:5][C:6]1[CH:7]=[C:8]([C:12]2[C:13]([Cl:23])=[CH:14][C:15]([C:19]([F:22])([F:20])[F:21])=[CH:16][C:17]=2[Cl:18])[CH:9]=[CH:10][C:11]=1[N+:1]([O-:4])=[O:2]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 221709261-Chloro-3-(2,6-dichloro-4-trifluoromethylphenyl)benzene

Product 1

HCID 221709381-Chloro-5-(2,6-dichloro-4-trifluoromethylphenyl)-2-nitrobenzeneYield 52.6%

Conditions

Temperature
5 °C

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.

Workup

  1. extractionextracted with 100 ml of diethyl ether twice
  2. washThe diethyl ether layer was washed with 200 ml of water twice
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe diethyl ether was distilled off under reduced pressure
  5. customPurification of the residue by silica gel column chromatography

Sources & evidence

ORD record
ord-06124b2381594664817937b62717d670
Source dataset
uspto-grants-2005_02
Patent number
US06858639B2

Reaction notes

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