Iodine → HCID 57692979, compound

HRID 545589Notes

Reaction equation

HRID 545589 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=1[F:20].[I:21]I.OS([O-])=O.[Na+]>S([O-])([O-])(=O)=O.[Ag+2].CO>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[C:16]([I:21])[C:15]([O:18][CH3:19])=[CH:14][C:13]=1[F:20]

Participants

6

Reactant 3

HCID 807IodineHCID 23665763Sodium BisulfiteHCID 57692980HCID 57692980, compound

Product 1

HCID 57692979HCID 57692979, compound

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 887MethanolSolvent

Procedure

Methyl 2-chloro-2′-fluoro-4′-methoxybiphenyl-4-carboxylate (550 mg, 1.87 mmol), methanol (8 mL), iodine (474 mg, 1.87 mmol), and silver sulfate (583 mg, 1.87 mmol) were stirred at room temperature for 2 hours to complete the reaction. The crude reaction mixture was worked up with NaHSO3 (aq). Volatiles were removed under reduced pressure. The pot residue was worked up with brine, extracted with ethyl acetate, dried over Na2SO4, filtered and evaporated to afford a light brown solid. This solid was purified on SiO2 (Biotage HorizonFlash system, 40+M cartridge, 0-20% EtOAc/hexanes, v/v) to afford the title compounds as a light yellow solid. LCMS calc.=419.94; found=420.86 (M+1)+.

Workup

  1. customthe reaction
  2. customThe crude reaction mixture
  3. customVolatiles were removed under reduced pressure
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customto afford a light brown solid
  9. customThis solid was purified on SiO2 (Biotage HorizonFlash system, 40+M cartridge, 0-20% EtOAc/hexanes

Sources & evidence

ORD record
ord-fa8f80524d2440b9a582b734cedc8cba
Source dataset
uspto-grants-2011_05
Patent number
US07935727B2

Reaction notes

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