Nitric Acid → 2,5-Difluoronitrobenzene

HRID 845337Notes

Reaction equation

HRID 845337 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.[N+:14]([O-])([OH:16])=[O:15]>>[F:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:8]=1[N+:14]([O-:16])=[O:15]

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 108921,4-Difluorobenzene

Product 1

HCID 677672,5-Difluoronitrobenzene

Procedure

To a cooled solution (0°-5° C./-15° C. with CO2 /acetone/water) of conc. sulfuric acid (600 ml) and 90% nitric acid (330 ml) in a three-necked flask equipped with a mechanical stirrer and thermometer was added 1,4-difluorobenzene dropwise (300 g., 2.63 moles) over 2.5 hours. After an additional 30 min. stirring, the mixture was carefully poured into ice and extracted with ethyl ether (3×600 ml). The organic layers were washed with brine, water, 5% sodium bicarbonate solution, dried over (Na2SO4) and evaporated in vacuo. The orange liquid was distilled under vacuum to obtain 1,4-difluoro-2-nitrobenzene, b.p. 102°-105° C. at 30 torr.

Workup

  1. additionthe mixture was carefully poured into ice
  2. extractionextracted with ethyl ether (3×600 ml)
  3. washThe organic layers were washed with brine, water, 5% sodium bicarbonate solution
  4. dry with materialdried over (Na2SO4)
  5. customevaporated in vacuo
  6. distillationThe orange liquid was distilled under vacuum

Sources & evidence

ORD record
ord-5682efa850f54121ab70415fc22e78d4
Source dataset
uspto-grants-1988_07
Patent number
US04758263

Reaction notes

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