Hydrochloric Acid → 1-Chloro-3-fluoro-2-nitrobenzene

HRID 1390371Notes

Reaction equation

HRID 1390371 reaction equation
Cl.[Cl:2][C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:4]=1N.Cl.[N+:12]([O-:15])([O-])=[O:13].[Na+].S([O-])([O-])(=O)=O>O>[Cl:2][C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:4]=1[N+:12]([O-:15])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1117Sulfate IonHCID 24268Sodium Nitrate2×HCID 203786572-Chloro-6-fluoroaniline hydrochloride

Product 1

HCID 30175001-Chloro-3-fluoro-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To a solution of 17.2 g. of 2-chloro-6-fluoroaniline hydrochloride and 12.5 ml. of concentrated hydrochloric acid in 150 ml. of water is added slowly a solution of 9 g. of sodium nitrate in 25 ml. of water. The temperature of the solution of kept below 5° at all times. This solution is then added to a stirred suspension of 18 g. of cuprocupric sulfate and 60 g. of sodium nitrate in 300 ml. of water at room temperature. The mixture is stirred for 1 hour then steam distilled until no trace of product is noted condensing in the distillate. The distillate is extracted with ether, dried (magnesium sulfate) concentrated and distilled to give 7.8 g. of product, b.p. 148°-152° at 30 mm. Gas chromatography analysis shows this to be greater than 95% pure.

Workup

  1. customThe temperature of the solution of kept below 5°
  2. additionThis solution is then added to a stirred suspension of 18 g
  3. customat room temperature
  4. distillationsteam distilled until no trace of product
  5. customcondensing in the distillate
  6. extractionThe distillate is extracted with ether
  7. dry with materialdried (magnesium sulfate)
  8. concentrationconcentrated
  9. distillationdistilled
  10. customto give 7.8 g

Sources & evidence

ORD record
ord-6e229d49fd244ae7873eadf95759c509
Source dataset
uspto-grants-1979_02
Patent number
US04138567

Reaction notes

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