1-(4-溴苯基)-2-氟乙酮

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 1-(4-bromophenyl)-2-fluoro-1-ethanone (3.54 g, 16.3 mmol) in tetrahydrofuran (50 ml) was added dropwise 1M lithium hexamethyldisilazide tetrahydrofuran solution (19.6 ml, 19.6 mmol) at −78° C. After stirring for 45 min., N-trifluoroacetylimidazole (2.3 ml, 19.6 mmol) was added. The resulting mixture was allowed to warm up to room temperature and stirred for 1.5 hr. The mixture was acidified with 2M hydrochloric acid and extracted with diethyl ether (300 ml). The separated organic layer was washed with water (100 ml×3) and dried over magnesium sulfate. The solution was evaporated to give 5.2 g of 1-(4-bromophenyl)-2,4,4,4-tetrafluoro-1,3-butanedione as a brown oil. This residue was heated with 5-hydrazino-2-pyrisinesulfonamide hydrochloride (1.10 g, 4.89 mmol) at refluxing temperature for 18 hr. After evaporation, the obtained residue was chromatographed on a column of silica gel (500 g) eluting with ethyl acetate/hexane (1:3 to 1:1) to afford 930 mg (12%) of the title compound as a yellow solid. stirred for 1.5 hr extracted with diethyl ether (300 ml) The separated organic layer was washed with water (100 ml×3) dried over magnesium sulfate The solution was evaporated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 2-bromo-1-(4-bromophenyl)-1-ethanone (8.54 g, 30.7 mmol), potassium fluoride (8.92 g, 153 mmol) and 18-crown-6 ether (4.06 g, 15.3 mmol) in acetonitrile (170 ml) was refluxed for 7 hr. After evaporation, the mixture was dissolved in ethyl acetate (300 ml), washed with water (100 ml×2), and dried over magnesium sulfate. Removal of solvent gave 6.8 g of brown solid, which was chromatographed on a column of silica gel (600 g) eluting with ethyl acetate/hexane (1:10) to afford 5.00 g (75%) of the title compound as a pale yellow solid. was refluxed for 7 hr After evaporation the mixture was dissolved in ethyl acetate (300 ml) washed with water (100 ml×2) dried over magnesium sulfate Removal of solvent

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 1-(4-bromophenyl)-2-fluoro-1-ethanone (3.54 g, 16.3 mmol) in tetrahydrofuran (50 ml) was added dropwise 1M lithium hexamethyldisilazide tetrahydrofuran solution (19.6 ml, 19.6 mmol) at −78° C. After stirring for 45 min., N-trifluoroacetylimidazole (2.3 ml, 19.6 mmol) was added. The resulting mixture was allowed to warm up to room temperature and stirred for 1.5 hr. The mixture was acidified with 2M hydrochloric acid and extracted with diethyl ether (300 ml). The separated organic layer was washed with water (100 ml×3) and dried over magnesium sulfate. The solution was evaporated to give 5.2 g of 1-(4-bromophenyl)-2,4,4,4-tetrafluoro-1,3-butanedione as a brown oil. This residue was heated with 5-hydrazino-2-pyrisinesulfonamide hydrochloride (1.10 g, 4.89 mmol) at refluxing temperature for 18 hr. After evaporation, the obtained residue was chromatographed on a column of silica gel (500 g) eluting with ethyl acetate/hexane (1:3 to 1:1) to afford 930 mg (12%) of the title compound as a yellow solid. stirred for 1.5 hr extracted with diethyl ether (300 ml) The separated organic layer was washed with water (100 ml×3) dried over magnesium sulfate The solution was evaporated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 2-bromo-1-(4-bromophenyl)-1-ethanone (8.54 g, 30.7 mmol), potassium fluoride (8.92 g, 153 mmol) and 18-crown-6 ether (4.06 g, 15.3 mmol) in acetonitrile (170 ml) was refluxed for 7 hr. After evaporation, the mixture was dissolved in ethyl acetate (300 ml), washed with water (100 ml×2), and dried over magnesium sulfate. Removal of solvent gave 6.8 g of brown solid, which was chromatographed on a column of silica gel (600 g) eluting with ethyl acetate/hexane (1:10) to afford 5.00 g (75%) of the title compound as a pale yellow solid. was refluxed for 7 hr After evaporation the mixture was dissolved in ethyl acetate (300 ml) washed with water (100 ml×2) dried over magnesium sulfate Removal of solvent

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 2-bromo-1-(4-bromophenyl)-1-ethanone (8.54 g, 30.7 mmol), potassium fluoride (8.92 g, 153 mmol) and 18-crown-6 ether (4.06 g, 15.3 mmol) in acetonitrile (170 ml) was refluxed for 7 hr. After evaporation, the mixture was dissolved in ethyl acetate (300 ml), washed with water (100 ml×2), and dried over magnesium sulfate. Removal of solvent gave 6.8 g of brown solid, which was chromatographed on a column of silica gel (600 g) eluting with ethyl acetate/hexane (1:10) to afford 5.00 g (75%) of the title compound as a pale yellow solid. was refluxed for 7 hr After evaporation the mixture was dissolved in ethyl acetate (300 ml) washed with water (100 ml×2) dried over magnesium sulfate Removal of solvent

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 1-(4-bromophenyl)-2-fluoro-1-ethanone (3.54 g, 16.3 mmol) in tetrahydrofuran (50 ml) was added dropwise 1M lithium hexamethyldisilazide tetrahydrofuran solution (19.6 ml, 19.6 mmol) at −78° C. After stirring for 45 min., N-trifluoroacetylimidazole (2.3 ml, 19.6 mmol) was added. The resulting mixture was allowed to warm up to room temperature and stirred for 1.5 hr. The mixture was acidified with 2M hydrochloric acid and extracted with diethyl ether (300 ml). The separated organic layer was washed with water (100 ml×3) and dried over magnesium sulfate. The solution was evaporated to give 5.2 g of 1-(4-bromophenyl)-2,4,4,4-tetrafluoro-1,3-butanedione as a brown oil. This residue was heated with 5-hydrazino-2-pyrisinesulfonamide hydrochloride (1.10 g, 4.89 mmol) at refluxing temperature for 18 hr. After evaporation, the obtained residue was chromatographed on a column of silica gel (500 g) eluting with ethyl acetate/hexane (1:3 to 1:1) to afford 930 mg (12%) of the title compound as a yellow solid. stirred for 1.5 hr extracted with diethyl ether (300 ml) The separated organic layer was washed with water (100 ml×3) dried over magnesium sulfate The solution was evaporated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 2-bromo-1-(4-bromophenyl)-1-ethanone (8.54 g, 30.7 mmol), potassium fluoride (8.92 g, 153 mmol) and 18-crown-6 ether (4.06 g, 15.3 mmol) in acetonitrile (170 ml) was refluxed for 7 hr. After evaporation, the mixture was dissolved in ethyl acetate (300 ml), washed with water (100 ml×2), and dried over magnesium sulfate. Removal of solvent gave 6.8 g of brown solid, which was chromatographed on a column of silica gel (600 g) eluting with ethyl acetate/hexane (1:10) to afford 5.00 g (75%) of the title compound as a pale yellow solid. was refluxed for 7 hr After evaporation the mixture was dissolved in ethyl acetate (300 ml) washed with water (100 ml×2) dried over magnesium sulfate Removal of solvent

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 1-(4-bromophenyl)-2-fluoro-1-ethanone (3.54 g, 16.3 mmol) in tetrahydrofuran (50 ml) was added dropwise 1M lithium hexamethyldisilazide tetrahydrofuran solution (19.6 ml, 19.6 mmol) at −78° C. After stirring for 45 min., N-trifluoroacetylimidazole (2.3 ml, 19.6 mmol) was added. The resulting mixture was allowed to warm up to room temperature and stirred for 1.5 hr. The mixture was acidified with 2M hydrochloric acid and extracted with diethyl ether (300 ml). The separated organic layer was washed with water (100 ml×3) and dried over magnesium sulfate. The solution was evaporated to give 5.2 g of 1-(4-bromophenyl)-2,4,4,4-tetrafluoro-1,3-butanedione as a brown oil. This residue was heated with 5-hydrazino-2-pyrisinesulfonamide hydrochloride (1.10 g, 4.89 mmol) at refluxing temperature for 18 hr. After evaporation, the obtained residue was chromatographed on a column of silica gel (500 g) eluting with ethyl acetate/hexane (1:3 to 1:1) to afford 930 mg (12%) of the title compound as a yellow solid. stirred for 1.5 hr extracted with diethyl ether (300 ml) The separated organic layer was washed with water (100 ml×3) dried over magnesium sulfate The solution was evaporated

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 1-(4-bromophenyl)-2-fluoro-1-ethanone (3.54 g, 16.3 mmol) in tetrahydrofuran (50 ml) was added dropwise 1M lithium hexamethyldisilazide tetrahydrofuran solution (19.6 ml, 19.6 mmol) at −78° C. After stirring for 45 min., N-trifluoroacetylimidazole (2.3 ml, 19.6 mmol) was added. The resulting mixture was allowed to warm up to room temperature and stirred for 1.5 hr. The mixture was acidified with 2M hydrochloric acid and extracted with diethyl ether (300 ml). The separated organic layer was washed with water (100 ml×3) and dried over magnesium sulfate. The solution was evaporated to give 5.2 g of 1-(4-bromophenyl)-2,4,4,4-tetrafluoro-1,3-butanedione as a brown oil. This residue was heated with 5-hydrazino-2-pyrisinesulfonamide hydrochloride (1.10 g, 4.89 mmol) at refluxing temperature for 18 hr. After evaporation, the obtained residue was chromatographed on a column of silica gel (500 g) eluting with ethyl acetate/hexane (1:3 to 1:1) to afford 930 mg (12%) of the title compound as a yellow solid. stirred for 1.5 hr extracted with diethyl ether (300 ml) The separated organic layer was washed with water (100 ml×3) dried over magnesium sulfate The solution was evaporated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 2-bromo-1-(4-bromophenyl)-1-ethanone (8.54 g, 30.7 mmol), potassium fluoride (8.92 g, 153 mmol) and 18-crown-6 ether (4.06 g, 15.3 mmol) in acetonitrile (170 ml) was refluxed for 7 hr. After evaporation, the mixture was dissolved in ethyl acetate (300 ml), washed with water (100 ml×2), and dried over magnesium sulfate. Removal of solvent gave 6.8 g of brown solid, which was chromatographed on a column of silica gel (600 g) eluting with ethyl acetate/hexane (1:10) to afford 5.00 g (75%) of the title compound as a pale yellow solid. was refluxed for 7 hr After evaporation the mixture was dissolved in ethyl acetate (300 ml) washed with water (100 ml×2) dried over magnesium sulfate Removal of solvent