Butyryl chloride → 4'-Methylbutyrophenone

Temperature

100 °C

p-Tolylboronic acid (0.150 g, 1.10 mmol), tetrakis(triphenylphosphine)palladium(0) (0.064 g, 0.055 mmol), and cesium carbonate (1.80 g, 5.52 mmol) were suspended in toluene (25 mL). The reaction mixture was purged under a vigorous flow of nitrogen for 15 minutes. Butyryl chloride (0.344 mL, 3.31 mmol) was added, and the reaction mixture was heated at 100° C. under an atmosphere of nitrogen for 24 h. The reaction mixture was cooled to ambient temperature and diluted with ether (100 mL). The organic layer was extracted sequentially with water (10 mL), aqueous sodium bicarbonate (10 mL), and aqueous sodium chloride (10 mL). The organic layer was dried (magnesium sulfate), filtered, and concentrated. Purification of the residue by flash column chromatography (7.5% ether/petroleum ether) afforded 1-(4-methylphenyl)-1-butanone as a colorless oil (0.134 g, 0.827 mmol): 1H NMR (CDCl3, 400 MHz) δ 7.86 (d, 2H), 7.25 (d, 2H), 2.92 (t, 2H), 2.41 (s, 3H), 1.76 (sx, 2H), 1.00 (t, 3H).

1. customThe reaction mixture was purged under a vigorous flow of nitrogen for 15 minutes
2. temperatureThe reaction mixture was cooled to ambient temperature
3. extractionThe organic layer was extracted sequentially with water (10 mL), aqueous sodium bicarbonate (10 mL), and aqueous sodium chloride (10 mL)
4. dry with materialThe organic layer was dried (magnesium sulfate)
5. filtrationfiltered
6. concentrationconcentrated
7. customPurification of the residue by flash column chromatography (7.5% ether/petroleum ether)

ORD record

ord-fb611cfad1204fce92670c8a728bdac2

Source dataset

uspto-grants-2005_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06921763B2