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

HRID 915610Notes

Reaction equation

HRID 915610 reaction equation
C1C(=O)N([I:8])C(=O)C1.[CH:9]1[C:14]([C:15]2[CH:16]=[CH:17][C:18]([F:22])=[CH:19][C:20]=2[F:21])=[CH:13][C:12]([C:23]([OH:25])=[O:24])=[C:11]([OH:26])[CH:10]=1.FC(F)(F)C(O)=O>C(#N)C>[F:21][C:20]1[CH:19]=[C:18]([F:22])[CH:17]=[CH:16][C:15]=1[C:14]1[CH:13]=[C:12]([C:23]([OH:25])=[O:24])[C:11]([OH:26])=[C:10]([I:8])[CH:9]=1

Participants

5

Reactant 3

HCID 3059DiflunisalHCID 6422Trifluoroacetic acidHCID 120273N-Iodosuccinimide

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

198 mg (0.88 mmol, 1.1 eq) of NIS was added at room temperature to a solution of 200 mg (0.8 mmol) of diflunisal in 4 ml of acetonitrile and a catalytic quantity of 18 μl (0.24 mmol, 0.3 eq) of trifluoroacetic acid. It was stirred continuously. The solvent was evaporated at low pressure, it was diluted with dichloromethane and the product was then worked up as in example 1.

Workup

  1. customThe solvent was evaporated at low pressure, it
  2. additionwas diluted with dichloromethane

Sources & evidence

ORD record
ord-fcc2cca221fa4cc59de07469d05413a2
Source dataset
uspto-grants-2007_09
Patent number
US07265245B2

Reaction notes

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