反应详情

A solution of 1-(4-fluoro-2-hydroxy-phenyl)-ethanone (15.4 g, Aldrich) in EtOAc (100 mL) was treated with AlCl3 (133 mg), stirred at r.t. for 30 min, treated with montmorillonite K10 (2.5 g) stirred an additional 30 min then treated with a solution of bromine (7.05 mL) in EtOAc (100 mL) (added dropwise via addition funnel over 1.5 h). The reaction was stirred at r.t. for 1 h, cooled in a an ice bath and quenched with water added dropwise. The mixture was diluted with EtOAc, filtered through celite and the filtrate was extracted with EtOAc (2×). The combined organic extracts were dried (Na2SO4), concentrated and teh crude product was purified via silica gel chromatography eluting with 5% EtOAc-hexanes to give 3.31 g of the title compound. MS (ESI) m/e 437(2M+H)+.

1. stirringstirred an additional 30 min
2. additionadded dropwise via addition funnel over 1.5 h)
3. stirringThe reaction was stirred at r.t. for 1 h
4. temperaturecooled in a an ice bath
5. customquenched with water
6. additionadded dropwise
7. additionThe mixture was diluted with EtOAc
8. filtrationfiltered through celite
9. extractionthe filtrate was extracted with EtOAc (2×)
10. dry with materialThe combined organic extracts were dried (Na2SO4)
11. concentrationconcentrated
12. customteh crude product was purified via silica gel chromatography
13. washeluting with 5% EtOAc-hexanes