Iodide Ion → HCID 57692979, compound

HRID 607106Notes

Reaction equation

HRID 607106 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].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 30165Iodide IonHCID 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), iodide (474 mg, 1.87 mmol) and silver sulfate (583 mg, 1.87 mmol) were stirred at room temperature for 2 hours. Reaction crude 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 by SiO2 (Biotage Horizon Flash system, 40+M cartridge, 0-20% EtOAc/hexanes, v/v) to afford the title compound. LCMS (ESI) calc.=419.94; found=420.86 (M+1)+.

Workup

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

Sources & evidence

ORD record
ord-c1a9a334836248408b08cd3fe387cf58
Source dataset
uspto-grants-2011_03
Patent number
US07915271B2

Reaction notes

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