Hydrochloric Acid → 4-Fluoro-2-iodobenzoic acid

HRID 2083762Notes

Reaction equation

HRID 2083762 reaction equation
[F:1][C:2]1[CH:3]=[C:4](N)[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].Cl.N([O-])=O.[Na+].[I-:17].[K+].S(=O)(=O)(O)O>O>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([I:17])[CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 4875Potassium IodideHCID 27249674-Fluoroanthranilic acidHCID 23668193Sodium Nitrite

Product 1

HCID 125201644-Fluoro-2-iodobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A mixture of 4.4 g. of 4-fluoroanthranilic acid in 35 ml. of water and 7 ml. of hyrochloric acid is diazotized with 2.0 g. of sodium nitrite in 6 ml. of water at 0°-5° C. The resulting cold solution is added dropwise to a mixture of 7.1 g. of potassium iodide, 2 ml. of sulfuric acid and 10 ml. of water. The mixture is heated for 2 hours to 100° C. and steam distilled. The cooled residue gives 4-fluoro-2-iodobenzoic acid, m.p. 140°-147° C.

Workup

  1. additionA mixture of 4.4 g
  2. customat 0°-5° C
  3. additionThe resulting cold solution is added dropwise to a mixture of 7.1 g
  4. temperatureThe mixture is heated for 2 hours to 100° C. and steam
  5. distillationdistilled

Sources & evidence

ORD record
ord-fa3c6b24178c4eab9ae2d7413d009601
Source dataset
uspto-grants-1978_04
Patent number
US04086350

Reaction notes

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