Benzeneacetyl chloride, 4-bromo- → 2-(4-Bromophenyl)-1-phenylethan-1-one

To a suspension of aluminum chloride (2.64 g, 19.8 mmol) in dry benzene (40 ml) was added a solution of 4-bromophenylacetyl chloride (4.63 g, 19.8 mmol) in 15 ml benzene over a period of 25 minutes under nitrogen. The resulting dark yellow solution was refluxed for six hours, and cooled to room temperature. Ice water (100 ml) was added, and the layers separated. The aqueous layer was extracted with benzene (1×50 ml). The combined organic portions were washed with water (2×60 ml), 10% NaOH (1×60 ml), water (1×60 ml), and brine (1×60 ml), and dried over magnesium sulfate. After filtration, concentration of the filtrate in vacuo afforded the ketone as 5.06 g of a white microcrystalline solid (93% yield). NMR indicated good purity. A portion was recrystallized from boiling petroleum ether/ethanol to give the ketone as colorless plates: m.p. 147.5-149.0° C. (lit. m.p. 146-147° C.; Huttel, R. et al., J. Chem. Ber. 93:1433 (1960)); 1H NMR δ8.02 (d, J=7.1 Hz, 2H), 7.63-7.46 (m, SH), 7.16 (d, J=8.3, 2H), 4.27 (s, 2H).

1. temperatureThe resulting dark yellow solution was refluxed for six hours
2. customthe layers separated
3. extractionThe aqueous layer was extracted with benzene (1×50 ml)
4. washThe combined organic portions were washed with water (2×60 ml), 10% NaOH (1×60 ml), water (1×60 ml), and brine (1×60 ml)
5. dry with materialdried over magnesium sulfate
6. filtrationAfter filtration, concentration of the filtrate in vacuo

ORD record

ord-f9a2af5216bc48ca89211bcbe6af5429

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06017910