Hydrochloric Acid → 2',4'-Difluoro-4-hydroxy-5-iodo-1,1'-biphenyl-3-carboxylic acid

HRID 915609Notes

Reaction equation

HRID 915609 reaction equation
[I-:1].[Na+].[OH-].[Na+].[CH:5]1[C:10]([C:11]2[CH:12]=[CH:13][C:14]([F:18])=[CH:15][C:16]=2[F:17])=[CH:9][C:8]([C:19]([OH:21])=[O:20])=[C:7]([OH:22])[CH:6]=1.Cl[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+].Cl>CO>[F:17][C:16]1[CH:15]=[C:14]([F:18])[CH:13]=[CH:12][C:11]=1[C:10]1[CH:9]=[C:8]([C:19]([OH:21])=[O:20])[C:7]([OH:22])=[C:6]([I:1])[CH:5]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 3059DiflunisalHCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 23665760Sodium Hypochlorite

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An equivalent of sodium iodide (165 mg, 1.1 mmol) and an equivalent of sodium hydroxide (32 mg) were added to a solution of 200 mg (0.80 mmol) of diflunisal in 5 ml of methanol. A 4% solution of sodium hypochlorite was dropwise added to the previous solution over a period of 75 min, keeping the temperature at 0-3° C. After every addition, a reddish colour was observed which quickly disappeared. It was stirred at this temperature for another hour and treated with a 20% aqueous solution of sodium thiosulphate. A 5% solution of HCl was added and it was extracted with dichloromethane. After the work-up, the product was recrystalized.

Workup

  1. customat 0-3° C
  2. additionAfter every addition
  3. extractionit was extracted with dichloromethane
  4. customAfter the work-up, the product was recrystalized

Sources & evidence

ORD record
ord-da979b9f5cc548d585381fb621fd9abb
Source dataset
uspto-grants-2007_09
Patent number
US07265245B2

Reaction notes

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