Reaction #1509626

Reaction equation

2,2,2-Trichloro-1-(4,5-dibromo-1-methyl-1H-pyrrol-2-yl)-ethanone

2,2,2-trichloro-1-(4,5-dibromo-1-methyl-pyrrol-2-yl)-ethanone

potassium carbonate

→

title compound

Yield 92.0%

4,5-dibromo-1-methyl-pyrrole-2-carboxylic acid methyl ester

Yield 92.0%

Solvents

methanol

Conditions

Workup

1. 1
   Otherwas quenched with water (10 mL)
2. 2
   OtherThe methanol was removed under reduced pressure
3. 3
   Otherthe residue partitioned between ethyl acetate (100 mL) and water (20 mL)
4. 4
   WashThe organic layer was subsequently washed with sat. NaHCO3 (2×30 mL), brine (2×20 mL)
5. 5
   Dryingdried over anhydrous sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   OtherEvaporation of the filtrate

Procedure

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.

Source