1-(4-bromophenyl)butan-1-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of hexamethyldisilazane (4.92 g, 30.5 mmol) in THF (10 ml) was added dropwise n-BuLi (1.57 M hexane solution, 19.4 ml, 30.5 mmol) at −78° C. and the mixture was stirred at room temperature for 15 minutes. The mixture was cooled down to −78° C. again and 1-(4-bromophenyl)-1-butanone (5.77 g, 25.4 mmol) in THF (25 ml) was added dropwise over 15 min. The resulting mixture was stirred at −78° C. for 30 minutes, then allowed to warm up to 0° C. and stirred for 40 minutes. The solution was recooled down to −78° C. and N-trifluoroacetylimidazole (5.00 g, 30.5 mmol) was added. The mixture was stirred at −78° C. for 20 minutes, and at room temperature for 2 hours. The reaction was quenched with 2N HCl (30 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (50 ml×2). The combined organic layer was washed with brine (50 ml), dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed over silica gel with hexane/ethyl acetate (8:1 to 3:1) to give 5.64 g (69%) of the title compound as a oil. The mixture was cooled down to −78° C. again The resulting mixture was stirred at −78° C. for 30 minutes to warm up to 0° C. stirred for 40 minutes was added The mixture was stirred at −78° C. for 20 minutes at room temperature for 2 hours The reaction was quenched with 2N HCl (30 ml) The organic layer was separated the aqueous layer was extracted with ethyl acetate (50 ml×2) The combined organic layer was washed with brine (50 ml) dried over Na2SO4 concentrated in vacuo The residue was chromatographed over silica gel with hexane/ethyl acetate (8:1 to 3:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-bromo-N-methoxy-N-methylbenzamide (13.4 g, 54.2 mmol) in THF (200 ml) was added n-PrMgBr (2M THF solution, 54.0 ml, 108 mmol) at 0° C. The mixture was stirred at room temperature for 45 minutes. Further n-PrMgBr (13.5 ml, 27.0 mmol) was added at 0° C., and the mixture was stirred at room temperature for 30 minutes. The excess reagent was quenched with saturated aqueous NH4Cl (200 ml), and ether (300 ml) was added. The organic layer was separated and the aqueous layer was extracted with ether (300 ml). The combined organic layer was washed with water (200 ml) and brine (200 ml), dried over Na2SO4, and concentrated in vacuo. The obtained residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (15:1) to give 10.1 g (82%) of the title compound as a yellow solid. the mixture was stirred at room temperature for 30 minutes The excess reagent was quenched with saturated aqueous NH4Cl (200 ml), and ether (300 ml) was added The organic layer was separated the aqueous layer was extracted with ether (300 ml) The combined organic layer was washed with water (200 ml) and brine (200 ml) dried over Na2SO4 concentrated in vacuo The obtained residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (15:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of hexamethyldisilazane (4.92 g, 30.5 mmol) in THF (10 ml) was added dropwise n-BuLi (1.57 M hexane solution, 19.4 ml, 30.5 mmol) at −78° C. and the mixture was stirred at room temperature for 15 minutes. The mixture was cooled down to −78° C. again and 1-(4-bromophenyl)-1-butanone (5.77 g, 25.4 mmol) in THF (25 ml) was added dropwise over 15 min. The resulting mixture was stirred at −78° C. for 30 minutes, then allowed to warm up to 0° C. and stirred for 40 minutes. The solution was recooled down to −78° C. and N-trifluoroacetylimidazole (5.00 g, 30.5 mmol) was added. The mixture was stirred at −78° C. for 20 minutes, and at room temperature for 2 hours. The reaction was quenched with 2N HCl (30 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (50 ml×2). The combined organic layer was washed with brine (50 ml), dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed over silica gel with hexane/ethyl acetate (8:1 to 3:1) to give 5.64 g (69%) of the title compound as a oil. The mixture was cooled down to −78° C. again The resulting mixture was stirred at −78° C. for 30 minutes to warm up to 0° C. stirred for 40 minutes was added The mixture was stirred at −78° C. for 20 minutes at room temperature for 2 hours The reaction was quenched with 2N HCl (30 ml) The organic layer was separated the aqueous layer was extracted with ethyl acetate (50 ml×2) The combined organic layer was washed with brine (50 ml) dried over Na2SO4 concentrated in vacuo The residue was chromatographed over silica gel with hexane/ethyl acetate (8:1 to 3:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-bromo-N-methoxy-N-methylbenzamide (13.4 g, 54.2 mmol) in THF (200 ml) was added n-PrMgBr (2M THF solution, 54.0 ml, 108 mmol) at 0° C. The mixture was stirred at room temperature for 45 minutes. Further n-PrMgBr (13.5 ml, 27.0 mmol) was added at 0° C., and the mixture was stirred at room temperature for 30 minutes. The excess reagent was quenched with saturated aqueous NH4Cl (200 ml), and ether (300 ml) was added. The organic layer was separated and the aqueous layer was extracted with ether (300 ml). The combined organic layer was washed with water (200 ml) and brine (200 ml), dried over Na2SO4, and concentrated in vacuo. The obtained residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (15:1) to give 10.1 g (82%) of the title compound as a yellow solid. the mixture was stirred at room temperature for 30 minutes The excess reagent was quenched with saturated aqueous NH4Cl (200 ml), and ether (300 ml) was added The organic layer was separated the aqueous layer was extracted with ether (300 ml) The combined organic layer was washed with water (200 ml) and brine (200 ml) dried over Na2SO4 concentrated in vacuo The obtained residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (15:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-bromo-N-methoxy-N-methylbenzamide (13.4 g, 54.2 mmol) in THF (200 ml) was added n-PrMgBr (2M THF solution, 54.0 ml, 108 mmol) at 0° C. The mixture was stirred at room temperature for 45 minutes. Further n-PrMgBr (13.5 ml, 27.0 mmol) was added at 0° C., and the mixture was stirred at room temperature for 30 minutes. The excess reagent was quenched with saturated aqueous NH4Cl (200 ml), and ether (300 ml) was added. The organic layer was separated and the aqueous layer was extracted with ether (300 ml). The combined organic layer was washed with water (200 ml) and brine (200 ml), dried over Na2SO4, and concentrated in vacuo. The obtained residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (15:1) to give 10.1 g (82%) of the title compound as a yellow solid. the mixture was stirred at room temperature for 30 minutes The excess reagent was quenched with saturated aqueous NH4Cl (200 ml), and ether (300 ml) was added The organic layer was separated the aqueous layer was extracted with ether (300 ml) The combined organic layer was washed with water (200 ml) and brine (200 ml) dried over Na2SO4 concentrated in vacuo The obtained residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (15:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of hexamethyldisilazane (4.92 g, 30.5 mmol) in THF (10 ml) was added dropwise n-BuLi (1.57 M hexane solution, 19.4 ml, 30.5 mmol) at −78° C. and the mixture was stirred at room temperature for 15 minutes. The mixture was cooled down to −78° C. again and 1-(4-bromophenyl)-1-butanone (5.77 g, 25.4 mmol) in THF (25 ml) was added dropwise over 15 min. The resulting mixture was stirred at −78° C. for 30 minutes, then allowed to warm up to 0° C. and stirred for 40 minutes. The solution was recooled down to −78° C. and N-trifluoroacetylimidazole (5.00 g, 30.5 mmol) was added. The mixture was stirred at −78° C. for 20 minutes, and at room temperature for 2 hours. The reaction was quenched with 2N HCl (30 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (50 ml×2). The combined organic layer was washed with brine (50 ml), dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed over silica gel with hexane/ethyl acetate (8:1 to 3:1) to give 5.64 g (69%) of the title compound as a oil. The mixture was cooled down to −78° C. again The resulting mixture was stirred at −78° C. for 30 minutes to warm up to 0° C. stirred for 40 minutes was added The mixture was stirred at −78° C. for 20 minutes at room temperature for 2 hours The reaction was quenched with 2N HCl (30 ml) The organic layer was separated the aqueous layer was extracted with ethyl acetate (50 ml×2) The combined organic layer was washed with brine (50 ml) dried over Na2SO4 concentrated in vacuo The residue was chromatographed over silica gel with hexane/ethyl acetate (8:1 to 3:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-bromo-N-methoxy-N-methylbenzamide (13.4 g, 54.2 mmol) in THF (200 ml) was added n-PrMgBr (2M THF solution, 54.0 ml, 108 mmol) at 0° C. The mixture was stirred at room temperature for 45 minutes. Further n-PrMgBr (13.5 ml, 27.0 mmol) was added at 0° C., and the mixture was stirred at room temperature for 30 minutes. The excess reagent was quenched with saturated aqueous NH4Cl (200 ml), and ether (300 ml) was added. The organic layer was separated and the aqueous layer was extracted with ether (300 ml). The combined organic layer was washed with water (200 ml) and brine (200 ml), dried over Na2SO4, and concentrated in vacuo. The obtained residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (15:1) to give 10.1 g (82%) of the title compound as a yellow solid. the mixture was stirred at room temperature for 30 minutes The excess reagent was quenched with saturated aqueous NH4Cl (200 ml), and ether (300 ml) was added The organic layer was separated the aqueous layer was extracted with ether (300 ml) The combined organic layer was washed with water (200 ml) and brine (200 ml) dried over Na2SO4 concentrated in vacuo The obtained residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (15:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of hexamethyldisilazane (4.92 g, 30.5 mmol) in THF (10 ml) was added dropwise n-BuLi (1.57 M hexane solution, 19.4 ml, 30.5 mmol) at −78° C. and the mixture was stirred at room temperature for 15 minutes. The mixture was cooled down to −78° C. again and 1-(4-bromophenyl)-1-butanone (5.77 g, 25.4 mmol) in THF (25 ml) was added dropwise over 15 min. The resulting mixture was stirred at −78° C. for 30 minutes, then allowed to warm up to 0° C. and stirred for 40 minutes. The solution was recooled down to −78° C. and N-trifluoroacetylimidazole (5.00 g, 30.5 mmol) was added. The mixture was stirred at −78° C. for 20 minutes, and at room temperature for 2 hours. The reaction was quenched with 2N HCl (30 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (50 ml×2). The combined organic layer was washed with brine (50 ml), dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed over silica gel with hexane/ethyl acetate (8:1 to 3:1) to give 5.64 g (69%) of the title compound as a oil. The mixture was cooled down to −78° C. again The resulting mixture was stirred at −78° C. for 30 minutes to warm up to 0° C. stirred for 40 minutes was added The mixture was stirred at −78° C. for 20 minutes at room temperature for 2 hours The reaction was quenched with 2N HCl (30 ml) The organic layer was separated the aqueous layer was extracted with ethyl acetate (50 ml×2) The combined organic layer was washed with brine (50 ml) dried over Na2SO4 concentrated in vacuo The residue was chromatographed over silica gel with hexane/ethyl acetate (8:1 to 3:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of hexamethyldisilazane (4.92 g, 30.5 mmol) in THF (10 ml) was added dropwise n-BuLi (1.57 M hexane solution, 19.4 ml, 30.5 mmol) at −78° C. and the mixture was stirred at room temperature for 15 minutes. The mixture was cooled down to −78° C. again and 1-(4-bromophenyl)-1-butanone (5.77 g, 25.4 mmol) in THF (25 ml) was added dropwise over 15 min. The resulting mixture was stirred at −78° C. for 30 minutes, then allowed to warm up to 0° C. and stirred for 40 minutes. The solution was recooled down to −78° C. and N-trifluoroacetylimidazole (5.00 g, 30.5 mmol) was added. The mixture was stirred at −78° C. for 20 minutes, and at room temperature for 2 hours. The reaction was quenched with 2N HCl (30 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (50 ml×2). The combined organic layer was washed with brine (50 ml), dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed over silica gel with hexane/ethyl acetate (8:1 to 3:1) to give 5.64 g (69%) of the title compound as a oil. The mixture was cooled down to −78° C. again The resulting mixture was stirred at −78° C. for 30 minutes to warm up to 0° C. stirred for 40 minutes was added The mixture was stirred at −78° C. for 20 minutes at room temperature for 2 hours The reaction was quenched with 2N HCl (30 ml) The organic layer was separated the aqueous layer was extracted with ethyl acetate (50 ml×2) The combined organic layer was washed with brine (50 ml) dried over Na2SO4 concentrated in vacuo The residue was chromatographed over silica gel with hexane/ethyl acetate (8:1 to 3:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-bromo-N-methoxy-N-methylbenzamide (13.4 g, 54.2 mmol) in THF (200 ml) was added n-PrMgBr (2M THF solution, 54.0 ml, 108 mmol) at 0° C. The mixture was stirred at room temperature for 45 minutes. Further n-PrMgBr (13.5 ml, 27.0 mmol) was added at 0° C., and the mixture was stirred at room temperature for 30 minutes. The excess reagent was quenched with saturated aqueous NH4Cl (200 ml), and ether (300 ml) was added. The organic layer was separated and the aqueous layer was extracted with ether (300 ml). The combined organic layer was washed with water (200 ml) and brine (200 ml), dried over Na2SO4, and concentrated in vacuo. The obtained residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (15:1) to give 10.1 g (82%) of the title compound as a yellow solid. the mixture was stirred at room temperature for 30 minutes The excess reagent was quenched with saturated aqueous NH4Cl (200 ml), and ether (300 ml) was added The organic layer was separated the aqueous layer was extracted with ether (300 ml) The combined organic layer was washed with water (200 ml) and brine (200 ml) dried over Na2SO4 concentrated in vacuo The obtained residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (15:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of hexamethyldisilazane (4.92 g, 30.5 mmol) in THF (10 ml) was added dropwise n-BuLi (1.57 M hexane solution, 19.4 ml, 30.5 mmol) at −78° C. and the mixture was stirred at room temperature for 15 minutes. The mixture was cooled down to −78° C. again and 1-(4-bromophenyl)-1-butanone (5.77 g, 25.4 mmol) in THF (25 ml) was added dropwise over 15 min. The resulting mixture was stirred at −78° C. for 30 minutes, then allowed to warm up to 0° C. and stirred for 40 minutes. The solution was recooled down to −78° C. and N-trifluoroacetylimidazole (5.00 g, 30.5 mmol) was added. The mixture was stirred at −78° C. for 20 minutes, and at room temperature for 2 hours. The reaction was quenched with 2N HCl (30 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (50 ml×2). The combined organic layer was washed with brine (50 ml), dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed over silica gel with hexane/ethyl acetate (8:1 to 3:1) to give 5.64 g (69%) of the title compound as a oil. The mixture was cooled down to −78° C. again The resulting mixture was stirred at −78° C. for 30 minutes to warm up to 0° C. stirred for 40 minutes was added The mixture was stirred at −78° C. for 20 minutes at room temperature for 2 hours The reaction was quenched with 2N HCl (30 ml) The organic layer was separated the aqueous layer was extracted with ethyl acetate (50 ml×2) The combined organic layer was washed with brine (50 ml) dried over Na2SO4 concentrated in vacuo The residue was chromatographed over silica gel with hexane/ethyl acetate (8:1 to 3:1)