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ChemicalBook CAS DataBase List 2-BROMO-5-ETHOXYPYRIDINE
42834-01-5

2-BROMO-5-ETHOXYPYRIDINE synthesis

3synthesis methods
-

Yield:42834-01-5 100%

Reaction Conditions:

Stage #1: 6-bromo-pyridin-3-olwith sodium hydride in N,N-dimethyl-formamide at 20; for 0.5 h;
Stage #2: ethyl iodide in N,N-dimethyl-formamide at 20; for 3.5 h;

Steps:

12.1

Reference Example 12 [0441] Step 1 [0442] To a solution of Compound vii-2 (2.0g, 11.49mmol) in DMF (20mL) was added sodium hydride (0.644g, 16.09mmol) at room temperature, and the mixture was stirred for 30 minutes. Iodoethane (1.858mL, 22.99mmol) was added to the mixture and the resulting mixture was stirred for additional 3.5 hours at room temperature. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed by water and brine, dried over anhydrous magnesium sulphate, and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give Compound vii-3 (2.32g, Yield 100%). [0443] 1H-NMR (CDCl3) δ: 8.03 (1H, d, J = 2.75 Hz), 7.35 (1H, d, J = 8.69 Hz), 7.07 (1H, dd, J = 8.62, 2.97 Hz), 4.05 (2H, q, J = 6.91 Hz), 1.43 (3H, t, J = 6.94 Hz).

References:

EP2752410,2014,A1 Location in patent:Paragraph 0441-0443

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