Methyl iodide → 2-Bromo-3-(methoxymethyl)pyridine

반응식

[Br:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].[CH3:12]I>O1CCCC1>[Br:1][C:2]1[C:7]([CH2:8][O:9][CH3:12])=[CH:6][CH:5]=[CH:4][N:3]=1

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온도: 0 °C

실험 절차

To a solution of (2-bromopyridin-3-yl)methanol (20 g, 106.37 mmoles) in 140 mL of tetrahydrofuran is added 60% sodium hydride in mineral oil (6.38 g, 155.5 mmol) at 0° C. under nitrogen atmosphere. Solution is stirred at 0° C. for 30 minutes. Methyl iodide (7.95 mL, 127.6 mmol) is added over the solution and the mixture is stirred at room temperature overnight. The mixture is quenched by addition of water and the crude is extracted with ethyl acetate. The organic layer is separated, dried over magnesium sulfate and solvent evaporated in vacuo to afford 2-bromo-3-(methoxymethyl)pyridin in a 98% yield that is used with no further purification. MS (m/z): 202 (M+1), 204 (M+3).