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反应机理
应用范围
反应条件温和，酯基不受影响，羧基α位不会发生消旋。
反应操作 Procedure for the conversion of aryl halides to phenols To a screw-cap vial or round bottom flask is added acetohydroxamic acid (3.0 equiv), powdered K2CO3 (5.0 equiv), aryl halide substrate (1.0 equiv), and DMSO such that the substrate concentration was 0.3- 0.6 M. In cases where the substrate is an oil, it is added by syringe or pipette after the DMSO is added. The vessel is sealed and heated at 80 o C for 2-18 h, and monitored for conversion by HPLC or TLC. At the end of the reaction, the mixture is cooled to rt and carefully quenched with approximately 9 equiv. of 2M HCl to a final pH of approximately 3-6. The aqueous phase is extracted 2 times with EtOAc and the product is purified by silica gel chromatography. In some cases, the product precipitates directly during the addition of HCl. In these cases, the solid is filtered and washed 3 times with water and dried under vacuum. |
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