4-Bromo-pyridine-2-carboxylic acid ethyl ester
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4-Bromo-pyridine-2-carboxylic acid ethyl ester
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CAS No:
62150-47-4
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Formula:
C8H8BrNO2
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Chemical Name:
4-Bromo-pyridine-2-carboxylic acid ethyl ester
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Synonyms:
4-Bromo-pyridine-2-carboxylic acid ethyl ester;Ethyl 4-bromopyridine-2-carboxylate;ethyl 4-broMopicolinate;2-Pyridinecarboxylic acid, 4-broMo-, ethyl ester
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CAS No:
4-Bromo-pyridine-2-carboxylic acid ethyl ester Use and Manufacturing
At -20 ° C ~ -10 ° C (preferably -10 ° C), 1700 g of ethyl pyruvate was dropped into 1400 g of 35percent hydrogen peroxide solution.The reaction was kept for 30 minutes and used.1400 g of 4-bromopyridine hydrochloride (Cpd 1) was added to ice water.At a temperature less than 10 ° C, Adjust the pH to 8-9 with potassium carbonateExtracted twice with 7L of dichloromethane (DCM).Dry; pour the above organic phase into a 50L reaction flask, Add 1.4 L of water to the reaction solution.4073g ferrous sulfate heptahydrate, 448mL concentrated sulfuric acid, Stir at room temperature;At -10 ° C to 0 ° C (preferably -5 ° C), Add ethyl pyruvate / hydrogen peroxide solution, Continue the reaction for 4 hours; extract with 7L of water, Spin dry to give ethyl 4-bromopyridine-2-carboxylate (Cpd 2)1390g.The yield was 82percent.To a stirred solutionof 4-bromopicolinic acid 4 (20 g, 87.33 mmol) in ethanol (250 mL) cooled to 5 °C, sulfuric acid (3 mL) was added and the reaction mixture was slowly cooled down to room temperature and then heated at 70 °C for 12 h. Upon completion of the reaction (TLC), the solvent was evaporated under vacuum. The residue was dissolved in ethyl acetate (500 mL), washed with ice cold water (100 mL), saturated by sodium bicarbonate solution (100 mL) and brine solution (100 mL). The organic layer was separated and dried over anhydrous sodium sulfate. The solvent was evaporated under vacuum and purified by column chromatography (hexane–ethyl acetate = 20 : 80) to give compound 5 (86 percent).
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4-Bromo-pyridine-2-carboxylic acid ethyl ester
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