Potassium Iodide → 3-Iodo-5-(methoxycarbonyl)benzoic acid

HRID 1592992Notes

Reaction equation

HRID 1592992 reaction equation
N[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].N([O-])=O.[Na+].[I-:19].[K+]>Cl.O>[I:19][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 135576433-Amino-5-(methoxycarbonyl)benzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 158403913-Iodo-5-(methoxycarbonyl)benzoic acidYield 55.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×

Procedure

To an ice-cold, stirred solution of commercially available 3-amino-5-(methoxycarbonyl)benzoic acid (5.19 g, 26.59 mmol) in 2 N hydrochloric acid (156 mL) was added a solution of sodium nitrite (1.84 g, 26.67 mmol) in water (10.8 mL). This mixture was then added dropwise to an ice-cold, stirred solution of potassium iodide (8.84 g, 53.25 mmol) in water (26.2 mL). After stirring for 35 min, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with 5% aqueous sodium thiosulfate, and saturated sodium chloride, dried (sodium sulfate), and concentrated under reduced pressure. Purification by flash column chromatography (silica, 50:50:2 hexanes/ethyl acetate/acetic acid) afforded the title compound (4.48 g, 55% yield) as an off-white solid. ESI-MS (m/z): 305 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with 5% aqueous sodium thiosulfate, and saturated sodium chloride
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash column chromatography (silica, 50:50:2 hexanes/ethyl acetate/acetic acid)

Sources & evidence

ORD record
ord-f95ee87fc6c347dd90c872a903474685
Source dataset
uspto-grants-2007_11
Patent number
US07294642B2

Reaction notes

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