Bromine → 2-bromo-4H,5H,6H-thieno(2,3-c)pyrrol-6-one

Temperature

0 °C

A solution of 4H-thieno[2,3-c]pyrrol-6(5H)-one (1.0 g, 7.2 mmol) in acetic acid (9 mL) and water (7 mL) was cooled to 0° C. Bromine (407 μL, 7.92 mmol) was added and the reaction was maintained at 0° C. for 1.5 h. At completion, water (30 mL) was added and the mixture was and extracted with EtOAc (2×50 mL). The combined organics were washed with 5% aq. Na2SO3 (30 mL), sat. aq. NaHCO3 (30 mL) and brine (30 mL), then dried over Na2SO4, filtered, concentrated. The crude material was purified by flash chromatography over silica gel (5% MeOH/DCM) to yield 2-bromo-4H-thieno[2,3-c]pyrrol-6(5H)-one (1.3 g, 83% yield) as a white solid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.28 (s, 1H), 4.39 (s, 3H); MS (EI) m/z=140.2 [M+1]+.

1. extractionextracted with EtOAc (2×50 mL)
2. washThe combined organics were washed with 5% aq. Na2SO3 (30 mL), sat. aq. NaHCO3 (30 mL) and brine (30 mL)
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated
6. customThe crude material was purified by flash chromatography over silica gel (5% MeOH/DCM)

ORD record

ord-94072797375042bf87e30cc33a010223

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08440652B2