ethyl 5-bromo-2-hydroxybenzoate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Ethyl 5-bromosalicylate (299 mg), 4-chloro-6,7-dimethoxyquinoline (270 mg), and 4-dimethylaminopyridine (440 mg) were suspended in o-dichlorobenzene (1 ml), and the suspension was stirred at 120° C. overnight. The reaction solution was cooled to room temperature, and the solvent was removed by distillation under the reduced pressure. Water was then added to the residue, and the mixture was extracted with chloroform. The chloroform layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-hexane to give the title compound (40 mg, yield 8%). The reaction solution was cooled to room temperature the solvent was removed by distillation under the reduced pressure Water was then added to the residue the mixture was extracted with chloroform The chloroform layer was washed with water was dried over anhydrous sodium sulfate The solvent was removed by distillation under the reduced pressure the residue was purified by column chromatography

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

実験手順: 5-Bromosalicylic acid (434 mg), 1-ethyl-3-(3-dimethylaminopropylcarbodiimide hydrochloride (420 mg), 1-hydroxybenzotriazole hydrate (337 mg), and ethanol (2 ml) were dissolved in N,N-dimethylformamide to prepare a solution which was then stirred at room temperature overnight. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-hexane to give ethyl 5-bromosalicylate (299 mg, yield 61%). to prepare a solution which the mixture was extracted with ethyl acetate The ethyl acetate layer was then washed with water was dried over anhydrous sodium sulfate The solvent was removed by distillation under the reduced pressure the residue was purified by column chromatography

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Ethyl 5-bromosalicylate (299 mg), 4-chloro-6,7-dimethoxyquinoline (270 mg), and 4-dimethylaminopyridine (440 mg) were suspended in o-dichlorobenzene (1 ml), and the suspension was stirred at 120° C. overnight. The reaction solution was cooled to room temperature, and the solvent was removed by distillation under the reduced pressure. Water was then added to the residue, and the mixture was extracted with chloroform. The chloroform layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-hexane to give the title compound (40 mg, yield 8%). The reaction solution was cooled to room temperature the solvent was removed by distillation under the reduced pressure Water was then added to the residue the mixture was extracted with chloroform The chloroform layer was washed with water was dried over anhydrous sodium sulfate The solvent was removed by distillation under the reduced pressure the residue was purified by column chromatography

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

実験手順: 5-Bromosalicylic acid (434 mg), 1-ethyl-3-(3-dimethylaminopropylcarbodiimide hydrochloride (420 mg), 1-hydroxybenzotriazole hydrate (337 mg), and ethanol (2 ml) were dissolved in N,N-dimethylformamide to prepare a solution which was then stirred at room temperature overnight. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-hexane to give ethyl 5-bromosalicylate (299 mg, yield 61%). to prepare a solution which the mixture was extracted with ethyl acetate The ethyl acetate layer was then washed with water was dried over anhydrous sodium sulfate The solvent was removed by distillation under the reduced pressure the residue was purified by column chromatography

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

実験手順: To 5-bromosalicylic acid (25 g, 115 mmol) in ethyl alcohol (300 mL) was added sulfuric acid (98%, 2 mL). The mixture was refluxed in a Dean-Stark apparatus for 2 days. The reaction mixture was cooled to room temperature. Most of the ethyl alcohol was removed by distillation. The residue was diluted with ethyl acetate, washed with water, aq. Na2CO3 and brine. The organic layer was dried (Na2SO4) and the solvent was removed to afford the title compound as a white solid. The mixture was refluxed in a Dean-Stark apparatus for 2 days Most of the ethyl alcohol was removed by distillation The residue was diluted with ethyl acetate washed with water, aq. Na2CO3 and brine The organic layer was dried (Na2SO4) the solvent was removed

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

実験手順: 5-Bromo-2-hydroxy-benzoic acid ethyl ester (40 g, 214 mmol) is suspended in sulfuric acid (200 mL) and the reaction cooled to zero in an ice bath. The reaction is equipped with an overhead stirrer and then the nitric acid (20 mL) in sulfuric acid (40 mL) is added dropwise to the solution over the course of 30 minutes. After the addition the ice bath is removed and the reaction warmed to room temperature. The reaction is stirred at room temperature for 16 hours. When complete the reaction is poured onto crushed ice and the resulting yellow solid is collected by vacuum filtration and washed with ice cold water. The solid dried in vacuum over overnight to give the 45 g (91%) of title compound that is used without further purification. LCMS (ESMS): m/z 291.1 (M+H+). the reaction cooled to zero in an ice bath The reaction is equipped with an overhead stirrer is removed When complete the reaction is poured onto crushed ice the resulting yellow solid is collected by vacuum filtration washed with ice cold water The solid dried in vacuum over overnight

反応条件: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Ethyl 5-bromosalicylate (299 mg), 4-chloro-6,7-dimethoxyquinoline (270 mg), and 4-dimethylaminopyridine (440 mg) were suspended in o-dichlorobenzene (1 ml), and the suspension was stirred at 120° C. overnight. The reaction solution was cooled to room temperature, and the solvent was removed by distillation under the reduced pressure. Water was then added to the residue, and the mixture was extracted with chloroform. The chloroform layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-hexane to give the title compound (40 mg, yield 8%). The reaction solution was cooled to room temperature the solvent was removed by distillation under the reduced pressure Water was then added to the residue the mixture was extracted with chloroform The chloroform layer was washed with water was dried over anhydrous sodium sulfate The solvent was removed by distillation under the reduced pressure the residue was purified by column chromatography

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

実験手順: 5-Bromosalicylic acid (434 mg), 1-ethyl-3-(3-dimethylaminopropylcarbodiimide hydrochloride (420 mg), 1-hydroxybenzotriazole hydrate (337 mg), and ethanol (2 ml) were dissolved in N,N-dimethylformamide to prepare a solution which was then stirred at room temperature overnight. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-hexane to give ethyl 5-bromosalicylate (299 mg, yield 61%). to prepare a solution which the mixture was extracted with ethyl acetate The ethyl acetate layer was then washed with water was dried over anhydrous sodium sulfate The solvent was removed by distillation under the reduced pressure the residue was purified by column chromatography