Acetic Anhydride → Ethyl 2',4'-difluoro-4-acetyloxy-5-iodo-[1,1']biphenyl-3-carboxylate

HRID 915617Notes

Reaction equation

HRID 915617 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:19]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:12]([OH:20])=[C:11]([I:21])[CH:10]=1.[C:22](OC(=O)C)(=[O:24])[CH3:23]>N1C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]([I:21])[C:12]([O:20][C:22](=[O:24])[CH3:23])=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:19]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 11407027Ethyl 5-(2,4-difluorophenyl)-3-iodo-salicylate

Product 1

HCID 11442200Ethyl 2',4'-difluoro-4-acetyloxy-5-iodo-[1,1']biphenyl-3-carboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 500 mg (1.24 mmol) of ethyl 5-(2,4-difluorophenyl)-3-iodo-salicylate (Example 10) in 12 ml of pyridine and 3 ml of acetic anhydride was heated in a water bath for 20 min. The mixture was allowed to cool and poured over ice and the product was extracted with dichloromethane. After drying the organic phase and after evaporating the solvent at low pressure, the crude was recrystalized.

Workup

  1. temperaturewas heated in a water bath for 20 min
  2. temperatureto cool
  3. additionpoured over ice
  4. extractionthe product was extracted with dichloromethane
  5. customAfter drying the organic phase
  6. customafter evaporating the solvent at low pressure
  7. customthe crude was recrystalized

Sources & evidence

ORD record
ord-01e5f2b5d5f34d26ab670de74d1af477
Source dataset
uspto-grants-2007_09
Patent number
US07265245B2

Reaction notes

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