Iodine → Methyl 4-bromo-5-iodothiophene-2-carboxylate

Participants

Reaction Steps

At −78° C., nBuLi (2.05 mL, 5.13 mmol) was added to a solution of methyl 4,5-dibromo-2-thiophenecarboxylate (1.4 g, 4.67 mmol) in THF (10 mL). After the mixture was stirred for 30 min, I2 (1.185 g, 4.67 mmol) was added in 3 mL THF. After the resulting solution was stirred at −78° C. for 1 h, it was quenched with Na2S2O3 at −78° C., and warmed to RT. The reaction mixture was extracted with DCM, dried over Na2SO4, and concentrated. The crude product was purified on silica (EtOAc/Hex, 0-10%) to give the title compound (1.3 g, 56%) as a yellow solid: LC-MS (ES) m/z 348(M+H)+.

Provenance & Evidence