Nitric Acid → 1,3-Bis(2,6-dichloro-alpha,alpha,alpha-trifluoro-p-tolyloxy)-4-nitrobenzene

HRID 65340Notes

Reaction equation

HRID 65340 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[Cl:10][C:11]1[CH:16]=[C:15]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]3[CH:30]=[C:29]([Cl:31])[C:28]([C:32]([F:35])([F:34])[F:33])=[C:27]([Cl:36])[CH:26]=3)[CH:19]=2)[CH:14]=[C:13]([Cl:37])[C:12]=1[C:38]([F:41])([F:40])[F:39]>ClCCCl>[Cl:10][C:11]1[CH:16]=[C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([N+:6]([O-:9])=[O:7])=[C:20]([O:24][C:25]3[CH:26]=[C:27]([Cl:36])[C:28]([C:32]([F:33])([F:34])[F:35])=[C:29]([Cl:31])[CH:30]=3)[CH:19]=2)[CH:14]=[C:13]([Cl:37])[C:12]=1[C:38]([F:41])([F:40])[F:39]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 867353071,3-Bis(2,6-dichloro-alpha,alpha,alpha-trifluoro-p-tolyloxy)-benzene

Product 1

HCID 867353061,3-Bis(2,6-dichloro-alpha,alpha,alpha-trifluoro-p-tolyloxy)-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A cooled mixture of concentrated sulfuric acid (6.5 ml.) and nitric acid (4.4 ml.) is added with stirring to an ice cold solution of 1,3-bis(2,6-dichloro-α,α,α-trifluoro-p-tolyloxy)-benzene (11.1 g. 0.021 mol) in 1,2-dichloroethane (30 ml.). After thirty minutes at room temperature, the phases are allowed to separate and the organic phase washed twice with water. Benzene (200 ml.) is added and the solution washed twice with dilute sodium carbonate solution, dried, filtered through activated silica gel (~25 g.), and the solvents removed. The residual crystals are triturated with pentane, filtered, and dried to obtain 1,3-bis(2,6-dichloro-α,α,α-trifluoro-p-tolyloxy)-4-nitrobenzene (9.9 g., 82%) m.p. 137.5°-140.5° C., 90% pure.

Workup

  1. additionis added
  2. waitAfter thirty minutes at room temperature
  3. customto separate
  4. washthe organic phase washed twice with water
  5. additionBenzene (200 ml.) is added
  6. washthe solution washed twice with dilute sodium carbonate solution
  7. customdried
  8. filtrationfiltered through activated silica gel (~25 g.)
  9. customthe solvents removed
  10. customThe residual crystals are triturated with pentane
  11. filtrationfiltered
  12. customdried

Sources & evidence

ORD record
ord-905ab4e857364bf09944b95bf6ce3aa1
Source dataset
uspto-grants-1986_09
Patent number
US04613360

Reaction notes

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