2-Amino-5-bromo-4-methylpyridine synthesis
- Product Name:2-Amino-5-bromo-4-methylpyridine
- CAS Number:98198-48-2
- Molecular formula:C6H7BrN2
- Molecular Weight:187.04
695-34-1
98198-48-2
General procedure for the synthesis of 2-amino-5-bromo-4-methylpyridine from 2-amino-4-methylpyridine: 2-amino-4-methylpyridine (0.5 mmol, 1.0 eq.), p-toluenesulfonic acid (p-TSA, 0.4 mmol, 0.8 eq.), and brominated 1-butylpyridine (1.5 mmol, 3.0 eq.) were added to a 50 mL Schlenk tube ) were added to the mixture. Under air atmosphere, 2-dimethoxyethane (2 mL) was added as solvent. Subsequently, hydrogen peroxide (H2O2, 1.2 mmol, 2.4 eq.) was slowly added to the reaction system. The reaction mixture was stirred at 80 °C for 24 hours. Upon completion of the reaction, the mixture was purified by silica gel column chromatography (eluent: petroleum ether/ethyl acetate) to afford the target product 2-amino-5-bromo-4-methylpyridine.
695-34-1
549 suppliers
$5.00/10g
98198-48-2
364 suppliers
$5.00/1g
Yield:98198-48-2 71%
Reaction Conditions:
with dihydrogen peroxide;1-butylpyridinium bromide;toluene-4-sulfonic acid in 1,2-dimethoxyethane at 80; for 24 h;Schlenk technique;Inert atmosphere;Green chemistry;regioselective reaction;
Steps:
General procedure for the bromination of 2-aminopyridines with 1-butylpyridinium bromide
General procedure: To a mixture of 2-aminopyridine (0.5 mmol, 1 equiv), p-TSA (0.4 mmol,0.8 equiv), 1-butylpyridinium bromide (1.5 mmol, 3 equiv) in a 50 mL Schlenk tube were added 1,2-dimethoxyethane (2 mL) under air. Then H2O2 (1.2 mmol, 2.4 equiv) was added. The mixture was stirred at 80°C for 24 h. And then the mixture was purified by silica gel column chromatography (petroleum ether/ethyl acetate) to give the products.
References:
Xu, Tong;Zhou, Wen;Wang, Jing;Li, Xue;Guo, Jun-Wen;Wang, Bin [Tetrahedron Letters,2014,vol. 55,# 36,p. 5058 - 5061] Location in patent:supporting information
5327-32-2
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98198-48-2
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$5.00/1g
142404-82-8
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98198-48-2
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$5.00/1g
695-34-1
549 suppliers
$5.00/10g
98198-48-2
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$5.00/1g
3430-29-3
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40073-38-9
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