反应详情

温度

-10 °C

To a solution of (2-bromo-5-chloro-4-(4-ethylbenzyl)phenyl)methanol (3.4 g, 10 mmol) in DMF (50 mL) was added NaH (0.8 g, 20 mmol, 60% in miner oil) in portions at −5° C. After being stirred for 1 h at the same temperature, the reaction mixture was cooled to −10° C., TBAI (0.37 g, 1 mmol) and a solution of allyl bromide (1.45 g, 12 mmol) in DMF (10 mL) was added. The reaction mixture was stirred for another 1 h prior to quenching by ice water and extracted 3× with EtOAc. The combined organic layers were washed with brine and then dried over Na2SO4. Concentration gave the crude product, which was purified by silica column chromatography (elution with PE:EtOAc=10:1) to afford the title compound (3.22 g, yield 84.8%).

1. stirringThe reaction mixture was stirred for another 1 h
2. customto quenching by ice water
3. extractionextracted 3× with EtOAc
4. washThe combined organic layers were washed with brine
5. dry with materialdried over Na2SO4
6. concentrationConcentration
7. customgave the crude product, which
8. customwas purified by silica column chromatography (elution with PE:EtOAc=10:1)