ChemicalBook CAS DataBase List 2-Fluoro-3-iodopyridine

2-Fluoro-3-iodopyridine synthesis

5synthesis methods

Product Name:2-Fluoro-3-iodopyridine
CAS Number:113975-22-7
Molecular formula:C5H3FIN
Molecular Weight:222.99

372-48-5 Synthesis

372-48-5
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113975-22-7
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$7.00/1g

Yield:113975-22-7 92%

Reaction Conditions:

Stage #1:2-fluoropyridine with n-butyllithium;diisopropylamine in tetrahydrofuran;hexane at -78; for 4 h;
Stage #2: with iodine in tetrahydrofuran;hexane at -78; for 1 h;

Steps:

1.a
(a) 222 mL of n-butyllithium (1.57 mol/L hexane solution) was dropwise added at -20°C to a solution having 34.2 g (340 mmol) of diisopropylamine dissolved in 400 mL of tetrahydrofuran, followed by stirring for 1 hour. The solution was cooled to -78°C, a solution having 32.0 g (330 mmol) of 2-fluoropyridine dissolved in 50 mL of tetrahydrofuran was added thereto, followed by stirring for 4 hours, and a solution having 87.1 g (341 mmol) of iodine dissolved in 150 mL of tetrahydrofuran was added thereto, followed by stirring for 1 hour. 200 mL of water was added to the mixture to terminate the reaction, and tetrahydrofuran was distilled off under reduced pressure. Extraction with ethyl ether was carried out, the organic layer was dried over anhydrous sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure, to obtain 67.4 g (crude yield 92%) of a crude product of 2-fluoro-3-iodopyridine.1H-NMR(CDCl3, 400 MHz) : δ (ppm) = 6.91-6.88(m,1H), 8.08-8.12(m,2H)

References:

ISHIHARA SANGYO KAISHA, LTD. EP1559320, 2005, A1 Location in patent:Page/Page column 6

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78607-36-0 Synthesis