Hydrochloric Acid → 3-Iodo-5-(methoxycarbonyl)benzoic acid

HRID 14291

Reaction equation

HRID 14291 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].Cl.N([O-])=O.[Na+].[I-:20].[K+]>O>[I:20][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 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 135576433-Amino-5-(methoxycarbonyl)benzoic acidHCID 23668193Sodium Nitrite

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

To an ice-cold, stirred solution of 3-amino-5-(methoxycarbonyl)benzoic acid (5.19 g, 26.59 mmol) in a 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 3-iodo-5-(methoxycarbonyl)benzoic acid (4.48 g): 1H NMR (500 MHz, DMSO-d6): δ 13.49 (br s, 1H), 8.45-8.38 (m, 3H), 3.83 (s, 3H); 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-b9e365e738df4d5f94ed7d7af91e7e2d
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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