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

HRID 498970Notes

Reaction equation

HRID 498970 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-5abdbc3797b249d49c739b8d42b2b248
Source dataset
uspto-grants-2010_08
Patent number
US07767626B2

Reaction notes

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