Methyl iodide → 6-Bromo-2-methylbenzo[B]thiophene

Temperature

0 °C

Into a stirred solution of diisopropylamine (1.45 mL, 10.3 mmol) and TMEDA (3.4 mL, 22.5 mmol) in THF (30 mL, freshly distilled) at −78° C. is added 1.6 M n-BuLi (7.0 mL, 11.2 mmol) via a syringe. The solution is warmed to 0° C. for 30 min and re-cooled to −78° C. A solution of 6-bromobenzo[b]thiophene 2.0 g, 9.38 mmol) in THF (10 mL) is added via a cannula. After stirring for 30 min, a solution of CH3I (14.0 mL, 28.1 mmol, 2.0 M in tert-butyl methyl ether) is added via a cannula. The solution is stirred overnight, while allowed to warm to room temperature, and diluted with saturated aqueous NaHCO3 (50 mL). The mixture is extracted with Et2O (3×50 mL). The organic layers are combined, dried over MgSO4, filtered and concentrated under reduced pressure to give the title compound as a tan solid (2.0177 g, 95%).

1. temperaturere-cooled to −78° C
2. stirringThe solution is stirred overnight
3. temperatureto warm to room temperature
4. extractionThe mixture is extracted with Et2O (3×50 mL)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure

ORD record

ord-9325051da5144ad2926d2a2174af973f

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07557103B2