Ethanol → Ethyl 5-(2,4-difluorophenyl)-3-iodo-salicylate

HRID 915613Notes

Reaction equation

HRID 915613 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:17]=[C:13]([C:14]([OH:16])=[O:15])[C:12]([OH:18])=[C:11]([I:19])[CH:10]=1.[CH2:20](O)[CH3:21]>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:17]=[C:13]([C:14]([O:16][CH2:20][CH3:21])=[O:15])[C:12]([OH:18])=[C:11]([I:19])[CH:10]=1

Participants

3

Reactant 2

HCID 702EthanolHCID 43695632',4'-Difluoro-4-hydroxy-5-iodo-1,1'-biphenyl-3-carboxylic acid

Product 1

HCID 11407027Ethyl 5-(2,4-difluorophenyl)-3-iodo-salicylate

Procedure

A solution of 5-(2,4-difluorophenyl)-3-iodo-salicylic acid (1.69 g, 4.61 mmol) in ethanol (20 ml) was cooled to 0° C. and a flow of anhydrous hydrochloride gas was bubbled through for 5 min. The solution was heated under reflux for 4 hr and cooled to room temperature, the solvents were evaporated at low pressure. The residue was dissolved in dichloromethane and the product was worked up. The reaction crude was purified by chromatography on silica gel using hexane/ethyl acetate (7:3) as the eluent.

Workup

  1. customa flow of anhydrous hydrochloride gas was bubbled through for 5 min
  2. temperatureThe solution was heated
  3. temperatureunder reflux for 4 hr
  4. customthe solvents were evaporated at low pressure
  5. dissolutionThe residue was dissolved in dichloromethane
  6. customThe reaction crude
  7. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-84bd7f872ca146aa90ae0e107d61cf87
Source dataset
uspto-grants-2007_09
Patent number
US07265245B2

Reaction notes

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