反应详情

3-Bromo-5-(bromomethyl)-2-fluoropyridine (5.63 g, 20.9 mmol) was dissolved in MeCN (135 mL) and 4-methoxybenzyl alcohol (5.20 mL, 41.9 mmol), silver (I) oxide (7.169 g, 30.9 mmol), and tetrabutylammonium iodide (2.208 g, 5.98 mmol) were added. The reaction flask was covered with aluminum foil and the reaction was stirred under nitrogen at room temperature overnight. The reaction was filtered through a pad of Celite® (diatomaceous earth), washing with DCM, MeOH and MeCN. The filtrate was concentrated and purified on a silica gel column (3:1 to 2:1 to 3:2 hexanes/DCM to 3:2 DCM/hexanes to 2:1 DCM/hexanes to 3:1 DCM/hexanes to DCM) to give 3-Bromo-2-fluoro-5-((4-methoxybenzyloxy)methyl)pyridine (1.62 g, 24%). MS (ESI pos. ion) m/z 326/328 (M+H)+.

1. filtrationThe reaction was filtered through a pad of Celite® (diatomaceous earth)
2. washwashing with DCM, MeOH and MeCN
3. concentrationThe filtrate was concentrated
4. custompurified on a silica gel column (3:1 to 2:1 to 3:2 hexanes/DCM to 3:2 DCM/hexanes to 2:1 DCM/hexanes to 3:1 DCM/hexanes to DCM)