2-Chloro-3-hydroxypyridine synthesis

9synthesis methods

Product Name:2-Chloro-3-hydroxypyridine
CAS Number:6636-78-8
Molecular formula:C5H4ClNO
Molecular Weight:129.54

2-CHLORO-3-PYRIDYL TRIFLUOROMETHANESULF&

163083-47-4

6636-78-8

GENERAL METHOD: To a solution of 2-chloro-3-pyridyl trifluoromethanesulfonate (0.3 mmol) in anhydrous toluene (5 mL) was added Cs2CO3 (3 equiv). The reaction suspension was heated at 80 °C (oil bath temperature) with stirring for 15 hours. Upon completion of the reaction, the crude reaction mixture was quenched with ethyl acetate (~5 mL) and saturated aqueous ammonium chloride solution (~10 mL). The aqueous layer was separated and extracted with ethyl acetate (2 x 10 mL). The organic layers were combined, dried with anhydrous MgSO4 and concentrated under reduced pressure to give the crude product 2-chloro-3-hydroxypyridine. Finally, the product was purified by fast column chromatography on silica gel.

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Yield:6636-78-8 95%

Reaction Conditions:

with caesium carbonate in toluene at 80; for 15 h;

Steps:

General procedure for deprotection of triflates
General procedure: Toa solution of aryl triflate 1a-k (0.3 mmol) in distilledtoluene (5 mL) was added Cs2CO3(3 eq.). The suspension was heated at 80 °C (oilbath temp) during 15h. The crude mixture was quenched withethyl acetate (~5 mL) and a saturatedaqueous solution of ammonium chloride (~10 mL).The aqueous layer was extracted with ethyl acetate (2x10 mL). Organic layerswere then combined, dried over MgSO4 and concentratedunder reduced pressure to afford the corresponding phenol 2a-k that was purified byflash chromatography over silica gel.

References:

Green, Alice E.;Agouridas, Vangelis;Deniau, Eric [Tetrahedron Letters,2013,vol. 54,# 51,p. 7078 - 7079] Location in patent:supporting information

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