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

HRID 372203Notes

Reaction equation

HRID 372203 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-:14])=[O:13].[Na+].S([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-:14])=[O:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1099SulfiteHCID 203786572-Chloro-6-fluoroaniline hydrochlorideHCID 23668193Sodium Nitrite2×

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 nitrite in 25 ml. of water. The temperature of the solution is kept below 5° at all times. This solution is then added to a stirred suspension of 18 g. of cuprocupric sulfite and 60 g. of sodium nitrite 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. customis kept below 5° at all times
  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-91f49ac798aa4662b0abf36a127eadf3
Source dataset
uspto-grants-1978_05
Patent number
US04089958

Reaction notes

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