Nitric Acid → 1-Chloro-2-fluoro-4-nitro-5-(trifluoromethyl)benzene

HRID 2417698

Reaction equation

HRID 2417698 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[CH:7]=[C:8]([C:13]([F:16])([F:15])[F:14])[CH:9]=[CH:10][C:11]=1[F:12]>>[Cl:5][C:6]1[C:11]([F:12])=[CH:10][C:9]([N+:1]([O-:4])=[O:2])=[C:8]([C:13]([F:14])([F:15])[F:16])[CH:7]=1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 157153Benzene, 2-chloro-1-fluoro-4-(trifluoromethyl)-

Product 1

HCID 201633061-Chloro-2-fluoro-4-nitro-5-(trifluoromethyl)benzene

Conditions

Temperature
40 °C

Procedure

About 500 parts of aqueous nitric acid was added slowly, with stirring, to a reaction vessel containing about 400 parts of 3-chloro-4-fluorobenzotrifluoride. The temperature of the reaction mixture was maintained at about 40° C. during the addition, then raised to about 60° C. and maintained thereat for about 5 hours. The reaction mixture was allowed to settle. The aqueous layer was removed and the organic layer was washed twice with 500 parts of water, treated several times with a saturated solution of sodium bicarbonate, washed with water again, dried over anhydrous magnesium sulfate, and filtered. The filtrate was distilled at reduced pressure to yield 347 parts of 5-chloro-4-fluoro-2-nitrobenzotrifluoride.

Workup

  1. temperatureraised to about 60° C.
  2. temperaturemaintained
  3. customThe aqueous layer was removed
  4. washthe organic layer was washed twice with 500 parts of water
  5. additiontreated several times with a saturated solution of sodium bicarbonate
  6. washwashed with water again
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. distillationThe filtrate was distilled at reduced pressure

Sources & evidence

ORD record
ord-d5e5dea3eb8046218951f189f2a249a1
Source dataset
uspto-grants-1984_09
Patent number
US04469893

Linked notes

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