反应详情

温度

60 °C

Sodium hydride (60% oil dispersion) (7.8 g) was added portionwise to a ice-water cooled solution of o-cresol (21.1 g) in tetrahydrofuran (500 mL). The mixture was stirred 20 minutes and then 1-(bromomethyl)-2-iodobenzene (58 g) was added. The mixture was warmed to 60° C. for 16 h. Additional sodium hydride (2 g) was added and the reaction mixture heated for an additional 3 h. The reaction mixture was cooled and carefully quenched with water and extracted with ethyl acetate (2×250 mL). The combined organic extracts were dried (Mg SO4), filtered and concentrated under reduced pressure to an oil, which was triturated with cold hexane to provide a solid which was collected by filtration to yield 59.1 g (94%) of the title compound of Step B as a white solid, mp 106°-108° C.

1. temperaturethe reaction mixture heated for an additional 3 h
2. temperatureThe reaction mixture was cooled
3. customcarefully quenched with water
4. extractionextracted with ethyl acetate (2×250 mL)
5. dry with materialThe combined organic extracts were dried (Mg SO4)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure to an oil, which
8. customwas triturated with cold hexane
9. customto provide a solid which
10. filtrationwas collected by filtration