Methanol → Methyl 5-(2,4-difluorophenyl)-3-iodo-salicylate

HRID 915614Notes

Reaction equation

HRID 915614 reaction equation
S(Cl)(Cl)=O.[F:5][C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:7]=1[C:13]1[CH:21]=[C:17]([C:18]([OH:20])=[O:19])[C:16]([OH:22])=[C:15]([I:23])[CH:14]=1.[CH3:24]O>>[F:5][C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:7]=1[C:13]1[CH:21]=[C:17]([C:18]([O:20][CH3:24])=[O:19])[C:16]([OH:22])=[C:15]([I:23])[CH:14]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 43695632',4'-Difluoro-4-hydroxy-5-iodo-1,1'-biphenyl-3-carboxylic acid

Product 1

HCID 11223005Methyl 5-(2,4-difluorophenyl)-3-iodo-salicylate

Procedure

11.5 ml of methanol and 2.9 ml of thionyl chloride (SOCl2) were placed in a flask under an inert atmosphere. It was stirred for 15 min and 1.67 g (4.56 mmol) of 5-(2,4-difluorophenyl)-3-iodo-salicylic acid was added. It was stirred continuously at room temperature until no evolution was observed by HPLC. The solvent was evaporated at low pressure and extraction was carried out with ethyl acetate. A crude of 97% purity was obtained and then purified by chromatography on silica gel.

Workup

  1. stirringIt was stirred continuously at room temperature until no evolution
  2. customThe solvent was evaporated at low pressure and extraction
  3. customA crude of 97% purity was obtained
  4. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-59e3d2ae053b4a8eae33e1d99e598390
Source dataset
uspto-grants-2007_09
Patent number
US07265245B2

Reaction notes

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