反应详情

温度

-50 °C

To a solution of 145 g (387 mmol) of 2-[(4-methoxybenzyl)oxy]-1-chloro-4-iodobenzene in 1.2 L of anhydrous THF, placed under argon and stirred at −50° C., are added dropwise 220 mL (440 mmol) of a 2N solution of iPrMgCl in THF, while maintaining the temperature between −40 and −50° C. The reaction mixture is allowed to warm to −10° C. and stirring is continued for 1 hour. 94 mL (406 mmol) of triisopropyl borate are then added and the reaction mixture is then allowed to warm slowly to 0° C. After stirring for 2 hours, the mixture is treated with 500 mL of aqueous 5N HCl solution and then extracted with ether (2×600 mL). The organic phase is washed with 2×1 L of water, dried over Na2SO4 and then concentrated under reduced pressure. The residue obtained is solidified in 300 mL of pentane, filtered off on a sinter funnel and washed with 200 mL of pentane. 96 g of [3-[(4-methoxybenzyl)oxy]-4-chlorophenyl]boronic acid are thus obtained in the form of a white solid.

1. temperaturewhile maintaining the temperature between −40 and −50° C
2. temperatureto warm to −10° C.
3. stirringstirring
4. temperatureto warm slowly to 0° C
5. stirringAfter stirring for 2 hours
6. extractionextracted with ether (2×600 mL)
7. washThe organic phase is washed with 2×1 L of water
8. dry with materialdried over Na2SO4
9. concentrationconcentrated under reduced pressure
10. customThe residue obtained
11. filtrationfiltered off on a sinter funnel
12. washwashed with 200 mL of pentane