Iodine → Methyl 4-(3-iodo-4-methoxyphenyl)-3-methylbenzoate

Participants

Reaction Steps

Methyl 4′-methoxy-2-methylbiphenyl-4-carboxylate (1.2 g, 4.68 mmol), methanol (20 mL), ethyl acetate (5 mL), iodine (1.19 g, 4.68 mmol), and silver sulfate (1.46 g, 4.68 mmol) were stirred at room temperature for 2 hours to complete the reaction. Volatiles were removed under reduced pressure to afford a yellow solid. The resulting solid was treated with brine followed by ethyl acetate extractions. The combined extracts were dried over Na2SO4 followed by filtration and concentration to afford a purple oil. The resulting oil was purified on SiO2 (Biotage HorizonFlash system, 40+M cartridge) to afford a white powder as the desired methyl 3′-iodo-4′-methoxy-2-methylbiphenyl-4-carboxylate. LCMS calc.=382.01; found=383.15 (M+1)+.

Provenance & Evidence