反应 #76285
ord-a5b93d68da6448919b73cc4727d101dc
反应方程式
反应物
反应条件
后处理
- 1干燥the resulting solution was dried by a Dean-Stark water separator (140-170° C.) for three hours
- 2温度This reaction mixture was cooled
- 3过滤filtered
- 4其他The organic layer was separated
- 5洗涤thoroughly washed with water
- 6干燥The resulting solution was dried with anhydrous magnesium sulfate
- 7浓缩concentrated
- 8其他the residue was purified by silica gel column chromatography (developing solvent; ethyl acetate:hexane=1:3)
- 9其他recrystallized from ethyl acetate-hexane
实验过程
To a mixture of 88.3 g (F.W. 235.46, 375 mmol) of 4-bromo-2-chlorobenzoic acid (3), 57.8 g (F.W. 154.165, 375 mmol) of 3,5-dimethoxyphenol (13), 93.2 g (F.W. 138.21, 670 mmol) of potassium carbonate and 400 mL of N-methyl-2-pyrrolidone was added benzene (200 mL), and the resulting solution was dried by a Dean-Stark water separator (140-170° C.) for three hours and then, 6.0 g (F.W. 63.55, 93.7 mmol) of copper (powder) and 17.8 g (F.W. 190.45, 93.7 mmol) of copper (I) iodide were added thereto and stirred at 120° C. for 30 minutes. This reaction mixture was cooled by standing and ice water and ethyl acetate were added thereto and then, the obtained solution was made pH 2 with concentrated hydrochloric acid and filtered. The organic layer was separated and then, thoroughly washed with water and subjected to salting out with a saturated sodium chloride aqueous solution. The resulting solution was dried with anhydrous magnesium sulfate and concentrated and the residue was purified by silica gel column chromatography (developing solvent; ethyl acetate:hexane=1:3) and recrystallized from ethyl acetate-hexane to obtain 75.4 g (57%) a desired compound (20). (TLC; ethyl acetate:hexane=1:2 or 1:1).