Hydrochloric Acid → 1-(4-Chloro-3-fluorophenyl)propan-2-one

Temperature

110 °C

To a mixture of 4-bromo-1-chloro-2-fluorobenzene (20.90 g, 100.0 mmol) and acetylacetone (30 mL, 300.0 mmol) in DMSO (100 mL) were added tripotassium phosphate (63.70 g, 300.0 mmol) and CuI (3.00 g, 15.80 mmol) under N2 and the mixture was stirred at 110° C. for 23 h. The mixture was cooled to rt and hydrochloric acid (300 mL, 2 M) was added. The resulting mixture was extracted with EtOAc (100 mL×3) and the combined organic phases were washed with brine (100 mL×2), dried over anhydrous Na2SO4 (50 g), and filtered. The filtrate was concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=10:1) to give the title compound as yellow liquid (9.02 g, 48.2%).

1. temperatureThe mixture was cooled to rt
2. extractionThe resulting mixture was extracted with EtOAc (100 mL×3)
3. washthe combined organic phases were washed with brine (100 mL×2)
4. dry with materialdried over anhydrous Na2SO4 (50 g)
5. filtrationfiltered
6. concentrationThe filtrate was concentrated in vacuo
7. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=10:1)

ORD record

ord-91ce1cfa23d94c04826d62bc2656608b

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434695B2