Potassium Carbonate → Methyl 4,5-Dibromo-1-Methylpyrrole-2-Carboxylate

2,2,2-trichloro-1-(4,5-dibromo-1-methyl-1H-pyrrol-2-yl)-ethanone 14 (1.00 g, 2.60 mmol), anhydrous potassium carbonate (0.719 g, 5.20 mmol), and anhydrous methanol (20 mL) were charged into a reaction flask. The resulting suspension was stirred for 16 h at room temperature upon which the reaction was quenched with water (10 mL). The methanol was removed under reduced pressure and the residue partitioned between ethyl acetate (100 mL) and water (20 mL). The organic layer was subsequently washed with sat. NaHCO3 (2×30 mL), brine (2×20 mL), dried over anhydrous sodium sulfate, and filtered. Evaporation of the filtrate yielded the title compound (0.710 g, 92%) as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 7.05 (s, 1H), 3.90 (s, 3H), 3.76 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 159.38, 123.62, 118.51, 113.93, 98.06, 51.58, 35.78; HRMS (FAB) calcd for C7H7Br2NO2 (M+) 294.8844, found 294.8861.

1. customwas quenched with water (10 mL)
2. customThe methanol was removed under reduced pressure
3. customthe residue partitioned between ethyl acetate (100 mL) and water (20 mL)
4. washThe organic layer was subsequently washed with sat. NaHCO3 (2×30 mL), brine (2×20 mL)
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationfiltered
7. customEvaporation of the filtrate

ORD record

ord-b34c1b820e494b8c842814b121c3bc53

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08653124B2