Iodide Ion → Methyl 2,2'-difluoro-5'-iodo-4'-methoxybiphenyl-4-carboxylate

HRID 607103Notes

Reaction equation

HRID 607103 reaction equation
[F: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]>S([O-])([O-])(=O)=O.[Ag+2].CO>[F: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

5

Reactant 2

HCID 30165Iodide IonHCID 57704854HCID 57704854, compound

Product 1

HCID 57704843Methyl 2,2'-difluoro-5'-iodo-4'-methoxybiphenyl-4-carboxylate

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 887MethanolSolvent

Procedure

methyl 2,2′-difluoro-4′-methoxybiphenyl-4-carboxylate (585 mg, 2.10 mmol), methanol (10 mL), iodide (534 mg, 2.10 mmol), silver sulfate (655 mg, 2.10 mmol) were stirred at room temperature. LCMS indicated formation of the desired compound. Reaction crude was worked up w/Na2HSO3 (aq., sat.). All volatiles were removed from the resulting mixture. The pot residue was worked up w/Na2SO4/EtOAc/filtration/concentration to afford a light brown solid. The crude solid was purified by flash chromatography (SiO2, Biotage 40+M cartridge). The column was eluted by a 0% to 20% EtOAc/hexanes mixture. 5 major fractions were spilled by accident. The remaining related fractions were pooled and concentrated in vacuo to afford the title compound. LCMS (ESI) calc.=403.97; found=404.92 (M+1)+.

Sources & evidence

ORD record
ord-f7d87cbdda0445f0991e79f99c26a5ef
Source dataset
uspto-grants-2011_03
Patent number
US07915271B2

Reaction notes

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