Acetone → 1-(3-Bromo-phenyl)-pentane-1,4-dione

A round bottom flask containing zinc chloride (71.95 mmol, 2.0 eq.) was heated under vacuum until the solid melted (˜300° C.) and the molten solid was kept under vacuum for 5 min. The molten solid was then allowed to cool to room temperature resulting in solidification. The flask was then filled with nitrogen and benzene (36 mL) was added followed by diethylamine (53.97 mmol, 1.5 eq.) and tert-butanol (53.97 mmol, 1.5 eq.). This mixture was stirred until the solid zinc chloride dissolved and then 3-bromophenacylbromide (35.98 mmol, 1.0 eq.) was added followed by acetone (53.97 mmol, 1.5 eq.). The resulting solution was stirred 4 d and quenched by the addition of 0.1N HCl (100 mL) and diluted with brine solution (25 mL) and extracted with ethyl acetate (3×75 mL). The combined organic layers were dried (MgSO4), filtered and concentrated to give an orange oil that was purified by column chromatography using 5% acetone/dichloromethane to give the final product as an orange solid (18.93 mmol, 53%). HRMS: calcd for C11H11BrO2+H+, 255.00152; found (ESI, [M+H]+ Obs'd), 255.0020.

1. temperaturewas heated under vacuum until the solid
2. custom(˜300° C.)
3. customresulting in solidification
4. additionwas added
5. dissolutiondissolved
6. customquenched by the addition of 0.1N HCl (100 mL)
7. additiondiluted with brine solution (25 mL)
8. extractionextracted with ethyl acetate (3×75 mL)
9. dry with materialThe combined organic layers were dried (MgSO4)
10. filtrationfiltered
11. concentrationconcentrated
12. customto give an orange oil that
13. customwas purified by column chromatography

ORD record

ord-878771c82da84eb298699b0abd0ad02d

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07947712B2