ChemicalBook CAS DataBase List 4-Iodo-2-(trifluoromethyl)pyridine

4-Iodo-2-(trifluoromethyl)pyridine synthesis

4synthesis methods

Product Name:4-Iodo-2-(trifluoromethyl)pyridine
CAS Number:590371-73-6
Molecular formula:C6H3F3IN
Molecular Weight:272.99

147149-98-2
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$30.00/1g

590371-73-6
108 suppliers
$18.00/250mg

Yield:590371-73-6 71%

Reaction Conditions:

with hydrogenchloride;sodium nitrite in water at 0 - 20; for 1.16667 h;

Steps:

8.1 Step-1: Synthesis of 4-iodo-2-(trifluoromethyl)pyridine

To a stirred solution of 2-(trifluoromethyl)pyridin-4-amine (1.0 g, 6.10 mmol, 1.0 eq.) in 5N HCl (10 mL) was added NaNO₂ (0.63 g, 0.91 mmol, 1.5 eq.) drop wise dissolved in water (10 mL) at 0° C. After 10 min KI (2.1 g, 12.8 mmol, 2.1 eq.) was added drop wise dissolved in (10 mL).
The reaction mixture was stirred at same temperature for 10 min and 1 h in RT.
Following this, reaction was allowed diluted with ethyl acetate (30 mL).
The aqueous layer was separated pH of aqueous layer was adjusted ?11 by adding 6N NaOH, the layers were separated and the organic layer was washed with 0.3M Na₂S₂O₃ (2*20 mL).
The combined organic layers were washed with brine (30 mL), dried over anhydrous Na₂SO₄, filtered and concentrated under vacuum to get the solid residue which was purified by was purified by normal phase silica-gel column chromatography to get the title compound as white solid (0.71 g, 71%). LCMS: 274.0 [M+1]⁺; ¹H NMR (400 MHz, DMSO-d₆) δ ppm 8.45 (d, J=4.89 Hz, 1H) 8.31 (s, 1H) 8.18 (d, J=4.89 Hz, 1H)