ChemicalBook CAS DataBase List PYRIDINE, 5-CHLORO-2-(PHENYLMETHOXY)-

PYRIDINE, 5-CHLORO-2-(PHENYLMETHOXY)- synthesis

4synthesis methods

Product Name:PYRIDINE, 5-CHLORO-2-(PHENYLMETHOXY)-
CAS Number:215437-47-1
Molecular formula:C12H10ClNO
Molecular Weight:219.67

16110-09-1
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100-51-6 Synthesis

100-51-6
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215437-47-1
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Yield:215437-47-1 91%

Reaction Conditions:

Stage #1: 2,5 dichloropyridine in N,N-dimethyl-formamide at 0; for 0.5 h;Inert atmosphere;
Stage #2: benzyl alcohol in N,N-dimethyl-formamide at 5;Inert atmosphere;

Steps:

129.1 Step 1 :

To a solution of 2,5-dichloropyridine (2 g, 13.51 mmol, 1.0 eq) in DMF (30 mL) under nitrogen atmosphere at 0 °C was added sodium hydride (0.65 g, 16.21 mmol, 1.2 eq) in portions. The mixture was stirred for 0.5 h and followed by addition of a solution of BnOH (1.75 g, 16.21 mmol, 1.2 eq) in DMF (2 mL). Then the resulting mixture was stirred at 5 °C overnight before it was diluted with water (90 mL) and extracted with EtOAc (3 x 90 mL). The combined organic layer was washed with brine, dried over NaiSCL, and concentrated. The crude residue was purified by flash column chromatography on silica gel (petroleum ether:EtOAc=100: l) to give 2-(benzyloxy)-5-chloropyridine (2.7 g, 91% yield).

References:

WO2020/186220,2020,A1 Location in patent:Paragraph 0293

4214-79-3 Synthesis