Acetone → 1-(5-Bromo-2-fluorophenyl)ethanone

To a 0° C. stirred solution of 5-bromo-2 fluoro-benzaldehyde (5.00 g, 24.6 mmol) in anhydrous ether (100 mL) under nitrogen gas was added via syringe MeMgBr (3M solution in ether, 10 mL, 30 mmol) over 3 min. The mixture was poured into a saturated solution of sodium bicarbonate (100 mL), the organic layer was separated and the aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated to give a viscous oil. The oil was mixed with acetone (100 mL) and treated with Jones reagent (1.1 M, 40 mL, 1.79 mmol). The mixture was stirred overnight, acetone was evaporated and the residue was extracted with ethyl acetate (60 mL×2). The extracts were washed with water (50 mL) and then a saturated aqueous solution of sodium bicarbonate (50 mL). Evaporation gave the ketone as an oil (4.63 g, 87%) that was used in the next reaction without further purification.

1. customthe organic layer was separated
2. extractionthe aqueous layer was extracted with ethyl acetate (100 mL)
3. dry with materialThe combined organic layers were dried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated
6. customto give a viscous oil
7. customacetone was evaporated
8. extractionthe residue was extracted with ethyl acetate (60 mL×2)
9. washThe extracts were washed with water (50 mL)
10. customEvaporation

ORD record

ord-2cdf806038044f4e80d2c4f07a28ddc4

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07655662B2