Iodine → HCID 18415139, compound

HRID 991984Notes

Reaction equation

HRID 991984 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].[I:13]I>C(O)(=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[C:6]([I:13])[C:7]=1[OH:8]

Participants

5

Reactant 2

HCID 807IodineHCID 1185343-Chloro-4-hydroxyphenylacetic acid

Product 1

HCID 18415139HCID 18415139, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 3-chloro-4-hydroxyphenylacetic acid (1.25 g) in glacial acetic acid (20 mL) was added 2.0 g of iodine crystals while stirring. The mixture was stirred in dark at ambient temperature for 2 days. The resulting mixture was diluted with water, extracted with ethyl acetate, dried and concentrated in vacuo to afford 3-chloro-5-iodo-4-hydroxyphenylacetic acid. This crude product was dissolved in methanol (30 mL), treated with concentrated sulfuric acid (2 mL) carefully, stirred at reflux for 20 h. Cooled reaction mixture was concentrated under reduced pressure, diluted with water, extracted with dichloromethane. The combined organic layers were dried and concentrated. Flash column chromatography on silica gel with ethyl acetate/hexane (0-50% gradient elution) afforded 3-chloro-5-iodo-4-hydroxyphenylacetic acid methyl ester (90 mg, 4%).

Workup

  1. stirringThe mixture was stirred in dark at ambient temperature for 2 days
  2. extractionextracted with ethyl acetate
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c78981ccb4be43f4b67e6715ae9f3ce3
Source dataset
uspto-grants-2002_10
Patent number
US06465687B1

Reaction notes

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