Potassium Iodide → 3-Chloro-2-iodobenzoic acid

HRID 1868834Notes

Reaction equation

HRID 1868834 reaction equation
N([O-])=O.[Na+].N[C:6]1[C:14]([Cl:15])=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9].[I-:16].[K+]>O.CS(C)=O.OS(O)(=O)=O>[Cl:15][C:14]1[C:6]([I:16])=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9]

Participants

7

Reactant 3

HCID 4875Potassium IodideHCID 808072-Amino-3-chlorobenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 144924693-Chloro-2-iodobenzoic acidYield 67.1%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A solution of sodium nitrite (4.82 g, 69.9 mmol) in water (25 mL) was added dropwise via addition funnel to a solution of 2-amino-3-chlorobenzoic acid (8.0 g, 46.6 mmol) in DMSO (25 mL) and 30% H2SO4 (75 mL) that had previously been cooled to 0° C. The mixture was stirred at 0° C. for 1 hour, at which time a solution of potassium iodide (19.3 g, 117 mmol) in water (25 mL) was added via addition funnel. The ice bath was removed, and the mixture was stirred for 2 hours. EtOAc (200 mL) was added, and the mixture was washed with 2N sodium sulfite (3×). The organic layer was then washed once with water and once with brine, dried over anhydrous MgSO4, and concentrated in vacuo to give 8.83 g of 3-chloro-2-iodobenzoic acid as a yellow solid.

Workup

  1. additionwas added via addition funnel
  2. customThe ice bath was removed
  3. additionEtOAc (200 mL) was added
  4. washthe mixture was washed with 2N sodium sulfite (3×)
  5. washThe organic layer was then washed once with water and once with brine
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-14abd758d56845e9946c2f0274e4fc43
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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