1H-Pyrrole-2-carboxylic acid, 4,5-dibromo-1-methyl- synthesis
- Product Name:1H-Pyrrole-2-carboxylic acid, 4,5-dibromo-1-methyl-
- CAS Number:66067-06-9
- Molecular formula:C6H5Br2NO2
- Molecular Weight:282.92
1198-71-6
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Yield:66067-06-9 94%
Reaction Conditions:
Stage #1: methyl 4,5-dibromo-1-methyl-1H-pyrrole-2-carboxylatewith methanol;lithium hydroxide;water in tetrahydrofuran at 20; for 16 h;
Stage #2: with hydrogenchloride;water pH=3;
Steps:
5
4,5-dibromo-1-methyl-pyrrole-2-carboxylic acid (15). 4,5-dibromo-1-methyl-1H-pyrrole-2-carboxylic acid methyl ester (0.675 g, 2.27 mmol), lithium hydroxide (0.436 g, 18.19 mmol), methanol (12 mL), tetrahydrofuran (4 mL), and water (4 mL) were stirred for 16 h at ambient temperature. The pH was then adjusted to 7.0 with an aqueous solution of 4N HCl. The organics were removed by rotary evaporation and the resulting residue diluted with water (15 mL). Acidification of the aqueous layer to pH=3 with 4N HCl afforded a white solid which was collected by vacuum filtration. The filter cake was rinsed with water (10 mL) to give the title compound 15 (0.601 g, 94%) as a white solid: 1H NMR (400 MHz, DMSO-d6) δ 12.83 (s, 1H), 7.00 (s, 1H), 3.90 (s, 3H); 13C NMR (100 MHz, DMSO-d6) δ 160.51, 124.74, 118.41, 113.07, 97.72, 35.64; HRMS (FAB) calcd for C6H5Br2NO2 (M+) 280.8687, found 280.8676.
References:
US2008/181923,2008,A1 Location in patent:Page/Page column 35; 40
6973-60-0
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865186-82-9
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96-54-8
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21898-65-7
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