Iodine → 2,4-Dichloro-5-iodobenzoic acid

HRID 1811722Notes

Reaction equation

HRID 1811722 reaction equation
I([O-])(=O)=O.[Na+].[I:6]I.[Cl:8][C:9]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12]>S(=O)(=O)(O)O>[Cl:8][C:9]1[CH:17]=[C:16]([Cl:18])[C:15]([I:6])=[CH:14][C:10]=1[C:11]([OH:13])=[O:12]

Participants

5

Reactant 3

HCID 807IodineHCID 57872,4-Dichlorobenzoic AcidHCID 23675764Sodium Iodate

Product 1

HCID 684179092,4-Dichloro-5-iodobenzoic acidYield 121.2%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Sodium iodate (4.4 g) and iodine (11.1 g) were added to 90% sulfuric acid (330 ml) and stirred at room temperature for 8 hours. Commercially available 2,4-dichlorobenzoic acid (21 g) was added and stirred at the same temperature for 24 hours. The reaction solution was poured onto ice water (3 l), and the precipitated solid material was separated by filtration. The solid material was then washed with water, and dried under reduced pressure. 2,4-Dichloro-5-iodobenzoic acid (16.8 g) was obtained by recrystallization (acetic acid-water). 2,4-Dichloro-5-iodobenzoic acid (2 g) was dissolved in dichloromethane (20 ml) and methanol (20 ml), and trimethylsilyldiazomethane (2 M; n-hexane solution) was added dropwise thereto until the solution became yellow. After a small amount of acetic acid was added, the mixture was concentrated under reduced pressure. The resulting residue was recrystallized from n-hexane to yield the title compound 2,4-dichloro-5-iodobenzoic acid methyl ester (2 g) as a white solid.

Workup

  1. stirringstirred at the same temperature for 24 hours
  2. additionThe reaction solution was poured onto ice water (3 l)
  3. customthe precipitated solid material was separated by filtration
  4. washThe solid material was then washed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-15cf147f042546a3b5ef67aef1907687
Source dataset
uspto-grants-2013_01
Patent number
US08362236B2

Reaction notes

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