Nitric Acid → 1-Chloro-2,5-difluoro-4-nitrobenzene

HRID 277413Notes

Reaction equation

HRID 277413 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[F:9].[N+:10]([O-])([OH:12])=[O:11]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:3]([F:9])=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 1375611-Chloro-2,5-difluorobenzene

Product 1

HCID 157514831-Chloro-2,5-difluoro-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
20 °C

Procedure

1-Chloro-2,5-difluorobenzene (31.7 g, 0.21 mol) was dissolved in sulfuric acid (110 ml) at −40° C., then a solution of sulfuric acid (20 ml) and nitric acid (30 ml) was added dropwise. The mixture was stirred for 1 hr while temperature slowly raised to 20° C. The product was forced to crystallize by mixing the reaction mixture with ice-water (500 ml), the yellow crystals were filtered, washed with cold water and dried in fume hood overnight. (38.0 g). 1H NMR (CDCl3, 300 MHz) 7.46 (1H, dd, J=9.8, 9.9 Hz), 7.96 (1H, dd, J=7.9, 7.9 Hz) ppm.

Workup

  1. customto crystallize
  2. additionby mixing the reaction mixture with ice-water (500 ml)
  3. filtrationthe yellow crystals were filtered
  4. washwashed with cold water
  5. customdried in fume hood overnight

Sources & evidence

ORD record
ord-f9bc6435248e4693b2f1bcdb7e34570a
Source dataset
uspto-grants-2002_03
Patent number
US06355799B1

Reaction notes

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