1-(Benzyloxy)-2-iodobenzene

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a 25 mL oven-dried flask was added Mg turnings (123 mg, 5.1 mmol) which was activated by the use of a heat-gun under vacuum. Under inert atmosphere was added a solution of 1-benzyloxy-2-iodo-benzene (25) (1.18 g, 3.8 mmol) in Et2O (10 mL) and the reaction mixture was allowed to reflux for 3.5 hours. A solution of 4-(4-n-butylpiperidin-1-yl)butanenitrile 4 (0.53 g, 2.5 mmol) dissolved in CH2Cl2 (3 mL) was added and the reaction mixture and was stirred at 40° C. over-night. The reaction mixture was quenched by addition of H2SO4 (10 mL, 2 M) and left stirring for 1 hour, followed by addition of NaOH (20 mL, 2 M) until basic conditions. The reaction mixture was extrated with ethyl acetate (3×50 mL)) and the combined organic phases are washed with brine (10 mL) and NaOH (10 mL, 2 M), and the combined organic phases were dried (MgSO4) and evaporated to dryness to produce 1.28 g of crude 26. The crude product was subjected to CC [eluent: Tol:EtOAc (1:1)] to give pure 26 (0.51 g, 51%); LC-MS [M+H]+ 393 (cald. 393.7). In a 25 mL oven-dried flask a heat-gun under vacuum to reflux for 3.5 hours was added The reaction mixture was quenched by addition of H2SO4 (10 mL, 2 M) left stirring for 1 hour followed by addition of NaOH (20 mL, 2 M) until basic conditions are washed with brine (10 mL) and NaOH (10 mL, 2 M) the combined organic phases were dried (MgSO4) evaporated to dryness to produce 1.28 g of crude 26

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a 25 mL ovendried flask 2-iodophenol (1.03 g, 4.7 mmol) and potassium carbonate (0.71 g, 5.2 mmol) were dissolved in dry acetone (10 mL). The mixture was stirred for 15 min followed by addition of benzylbromide (0.61 mL, 5.2 mmol) and left over-night at rt. Addition of H2O (50 mL) followed by extraction with ethyl acetate (3×50 mL) and the combined organic phases were dried (MgSO4) and evaporated to dryness, to produce 1.7 g of crude 25. The crude product was subjected to CC [eluent: Heptane:EtOAc (9:1)] to give pure 25 (1.2 g, 81%). LC-MS [M+H]+ 310 (cald. 310.0). left over-night at rt followed by extraction with ethyl acetate (3×50 mL) the combined organic phases were dried (MgSO4) evaporated to dryness to produce 1.7 g of crude 25

反応条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a 25 mL oven-dried flask was added Mg turnings (123 mg, 5.1 mmol) which was activated by the use of a heat-gun under vacuum. Under inert atmosphere was added a solution of 1-benzyloxy-2-iodo-benzene (25) (1.18 g, 3.8 mmol) in Et2O (10 mL) and the reaction mixture was allowed to reflux for 3.5 hours. A solution of 4-(4-n-butylpiperidin-1-yl)butanenitrile 4 (0.53 g, 2.5 mmol) dissolved in CH2Cl2 (3 mL) was added and the reaction mixture and was stirred at 40° C over-night. The reaction mixture was quenched by addition of H2SO4 (10 mL, 2 M) and left stirring for 1 hour, followed by addition of NaOH (20 mL, 2 M) until basic conditions. The reaction mixture was extrated with ethyl acetate (3×50 mL)) and the combined organic phases are washed with brine (10 mL) and NaOH (10 mL, 2 M), and the combined organic phases were dried (MgSO4) and evaporated to dryness to produce 1.28 g of crude 26. The crude product was subjected to CC [eluent: Tol: EtOAc (1:1)] to give pure 26 (0.51 g, 51%); LC-MS [M +H]+ 393 (cald. 393.7). In a 25 mL oven-dried flask a heat-gun under vacuum to reflux for 3.5 hours was added The reaction mixture was quenched by addition of H2SO4 (10 mL, 2 M) left stirring for 1 hour followed by addition of NaOH (20 mL, 2 M) until basic conditions are washed with brine (10 mL) and NaOH (10 mL, 2 M) the combined organic phases were dried (MgSO4) evaporated to dryness to produce 1.28 g of crude 26

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a 25 mI ovendried flask 2-iodophenol (1.03 g, 4.7 mmol) and potassium carbonate (0.71 g, 5.2 mmol) were dissolved in dry acetone (10 mL). The mixture was stirred for 15 min followed by addition of benzylbromide (0.61 mL, 5.2 mmol) and left over-night at rt. Addition of H20 (50 mL) followed by extraction with ethyl acetate (3×50 mL) and the combined organic phases were dried (MgSO4) and evaporated to dryness, to produce 1.7 g of crude 25. The crude product was subjected to CC [eluent:Heptane: EtOAc (9:1)] to give pure 25 (1.2 g, 81%). LC-MS [M+H]+ 310 (cald. 310.0). left over-night at rt Addition of H20 (50 mL) followed by extraction with ethyl acetate (3×50 mL) the combined organic phases were dried (MgSO4) evaporated to dryness to produce 1.7 g of crude 25