Bromine → 2-Bromo-5-methyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine

Temperature

0 °C

Bromine (0.3 mL) in HOAc (10 mL) was slowly added over 5 min to a mixture of 5-methyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (1.0 g, 6.5 mmol) in acetic acid (10 mL) and water (10 mL) at 0° C. The resulting mixture was stirred at 0° C. for 1 h. Work-up: the reaction mixture was partitioned between ethyl acetate (300 mL) and water (200 mL). The organic layer was separated, washed with saturated aqueous NaHCO3 (300 mL) and brine (100 mL), dried over Na2SO4, and concentrated in vacuo. The residue was recrystallized from 1:4 EtOAc/petroleum ether (150 mL) to afford the title compound as white solid (660 mg, 43%). 1H NMR (DMSO-d6, 400 MHz): δ 6.91 (s, 1H), 3.33 (s, 2H), 2.73-2.71 (m, 2H), 2.52-2.51 (m, 2H), 2.33 (s, 3H). LCMS: 233 (M+H)+.

1. customthe reaction mixture was partitioned between ethyl acetate (300 mL) and water (200 mL)
2. customThe organic layer was separated
3. washwashed with saturated aqueous NaHCO3 (300 mL) and brine (100 mL)
4. dry with materialdried over Na2SO4
5. concentrationconcentrated in vacuo
6. customThe residue was recrystallized from 1:4 EtOAc/petroleum ether (150 mL)

ORD record

ord-bebb8b6421ce432697fae79a8143408f

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09399646B2