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

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)+.

1. stirringAfter the resulting solution was stirred at −78° C. for 1 h
2. customit was quenched with Na2S2O3 at −78° C.
3. extractionThe reaction mixture was extracted with DCM
4. dry with materialdried over Na2SO4
5. concentrationconcentrated
6. customThe crude product was purified on silica (EtOAc/Hex, 0-10%)

ORD-Eintrag

ord-d6434ffc9b3e49fbbb3d1e7c39ceb360

Quelldatensatz

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08273782B2