Methanol → 5-Chloro-2-hydroxy-3-iodo-benzoic acid methyl ester

HRID 1197998Notes

Reaction equation

HRID 1197998 reaction equation
S(Cl)(Cl)=O.[CH3:5]O.[Cl:7][C:8]1[CH:16]=[C:12]([C:13]([OH:15])=[O:14])[C:11]([OH:17])=[C:10]([I:18])[CH:9]=1>CCOC(C)=O>[Cl:7][C:8]1[CH:16]=[C:12]([C:13]([O:15][CH3:5])=[O:14])[C:11]([OH:17])=[C:10]([I:18])[CH:9]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 929387HCID 929387, compound

Product 1

HCID 118231225-Chloro-2-hydroxy-3-iodo-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Thionyl chloride (30 mL, 411 mmol) is added dropwise to methanol (100 mL) in an ice bath. The addition is controlled to hold the temperature at 25° C. Upon completion of the addition 6 (25 g, 84 mmol) is added and the reaction heated to reflux for 4 hours. The solids dissolve at first then after 2 hours solids start to come out of solution. After 4 hours TLC (hex: EtOAc; 9:1) shows no starting material. The reaction is cooled in the refrigerator for 12h. The solids formed are filtered washed with water (30 mL), and dried under vacuum at 27° C. to yield methyl 5-chloro-3-iodosalicylate as an off white solid. (mp 143°-145° C.)

Workup

  1. additionThe addition
  2. customat 25° C
  3. additionis added
  4. temperaturethe reaction heated
  5. temperatureto reflux for 4 hours
  6. dissolutionThe solids dissolve at first then after 2 hours solids
  7. temperatureThe reaction is cooled in the refrigerator for 12h
  8. customThe solids formed
  9. filtrationare filtered
  10. washwashed with water (30 mL)
  11. customdried under vacuum at 27° C.

Sources & evidence

ORD record
ord-ccc811f165e6416d8771c95a2767fbf8
Source dataset
uspto-grants-1994_01
Patent number
US05278323

Reaction notes

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