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ChemicalBook CAS DataBase List 5-Bromo-3-fluoro-pyridine-2-carbonitrile
886373-28-0

5-Bromo-3-fluoro-pyridine-2-carbonitrile synthesis

5synthesis methods
5-Bromo-3-fluoro-2-pyridinecarbonitrile is an off-white to pale yellow solid, commonly used as an intermediate in organic synthesis, such as the synthesis of 5-bromo-3-methoxypyridine-2-carbonitrile
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Yield:886373-28-0 73%

Reaction Conditions:

Stage #1:5-bromo-3-fluoro-pyridine-2-carboxylic acid amide with sodium chloride;trichlorophosphate in dichloromethaneHeating / reflux;
Stage #2: with sodium hydrogencarbonate in dichloromethane;water at 20;

Steps:


Stir amixture of S-bromo-S-fluoro-pyridine^-carboxylic acid amide (0.375 mg, 1.71 mmol) and NaCl (0.120 g, 2.05 mmol) in CH2Cl2 (20 ml). After 15 minutes, addPOCl3 (0.795 ml, 8.55 mmol) and reflux the mixture overnight. Cool the mixture to room temperature, and dilute with CH2Cl2; wash with saturated NaHCO3 solution, dry(MgSO^. Purify the crude product using silica chromatography (0-50% EtOAc/Hexane) to produce 0.25 g (73% yield) of 5-bromo-2-cyano-3- fluoro-pyridine.

References:

ELI LILLY AND COMPANY WO2007/87488, 2007, A2 Location in patent:Page/Page column 23

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