Iodide Ion → Methyl 2'-fluoro-5'-iodo-4'-methoxy-3-methylbiphenyl-4-carboxylate

HRID 2093215Notes

Reaction equation

HRID 2093215 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[C:12]([CH3:20])[CH:11]=1.[I-:21]>S([O-])([O-])(=O)=O.[Ag+2].CO>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([I:21])=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[C:12]([CH3:20])[CH:11]=1

Participants

5

Reactant 2

HCID 30165Iodide IonHCID 57704853Methyl 2'-fluoro-4'-methoxy-3-methylbiphenyl-4-carboxylate

Product 1

HCID 57704857Methyl 2'-fluoro-5'-iodo-4'-methoxy-3-methylbiphenyl-4-carboxylate

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 887MethanolSolvent

Procedure

methyl 2′-fluoro-4′-methoxy-3-methylbiphenyl-4-carboxylate (100 mg, 0.365 mmol), methanol (3 mL), iodide (93 mg, 0.366 mmol) and silver sulfate (114 mg, 0.366 mmol) were stirred at room temperature for 1.5 hours. Reaction crude was quenched by Na2SO3 (sat., aq.). Volatiles were removed from the grayish brown mixture. The pot residue was worked up with H2O/EtOAc/Na2SO4/filtration/concentration to afford the title compound. LCMS (ESI) calc.=400.00; found=400.96 (M+1)+.

Workup

  1. customReaction crude
  2. customwas quenched by Na2SO3 (sat., aq.)
  3. customVolatiles were removed from the grayish brown mixture
  4. concentrationThe pot residue was worked up with H2O/EtOAc/Na2SO4/filtration/concentration

Sources & evidence

ORD record
ord-a7351fc43371436a854e1fd6028cd7e8
Source dataset
uspto-grants-2013_05
Patent number
US08440702B2

Reaction notes

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