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ChemicalBook CAS DataBase List 5-BROMOPYRIDINE-2-CARBOXYLIC ACID METHYL ESTER

5-BROMOPYRIDINE-2-CARBOXYLIC ACID METHYL ESTER synthesis

10synthesis methods
-

Yield:29682-15-3 92%

Reaction Conditions:

with sulfuric acid at 0 - 70; for 6 h;

Steps:

12 Synthesis of methyl 5-bromopicolinate (12.5).
To a solution of 5-bromopicolinic acid (12.6, 6.0 g, 29.9 mmol) in methanol (60 mL), sulfuric acid (3.0 mL) was added at 0 °C and the reaction mixture was heated at 70 °C for 6 h. After completion, cooled the mixture to room temperature and methanol was removed under reduced pressure. To the mixture, water (50 mL) was added and pH was adjusted to 6 by a solution of sodium bicarbonate .The product was extracted with ethyl acetate (200 mL), the organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude product was purified by washings with diethyl ether and pentane to afford methyl 5-bromopicolinate (12.5) as white solid. Yield: 6.0 g, 92.0%.

References:

ADHAERE PHARMACEUTICALS, INC.;BARBOSA, Antonio J. WO2018/126072, 2018, A1 Location in patent:Paragraph 0246; 0247

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