1-Phenyl-1-propanone → 2-(2-Methylphenyl)-1-phenylpropan-1-one

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Reaction Steps

An oven dried Schlenk tube equipped with a rubber septum was cooled under an argon purge. The septum was removed and the tube was charged with palladium acetate (2.3 mg, 0.01 mmol) and sodium t-butoxide (125 mg, 1.3 mmol). The tube was capped with the septum, purged with argon. Toluene (2 mL) was added and the mixture stirred for 1 min at room temperature. 3-Bromotoluene (0.120 mL, 1.0 mmol) and propiophenone (0.16 mL, 1.2 mmol) were added to the tube. The mixture was heated to 80° C. and stirred until the starting halide had been completely consumed, as judged by GC analysis. The mixture was cooled to room temperature, quenched with saturated aqueous ammonium chloride (10 mL) and diluted with ether (20 mL). The mixture was poured into a separatory funnel and the layers were separated. The aqueous layer was extracted with ether (20 mL), the combined organic layers were washed with brine (20 mL), dried over anhydrous magnesium sulfate filtered and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel to afford 103 mg (46%) of α-(2-Methylphenyl)propiophenone. 1H NMR (CDCl3, 300 MHz) 7.81-7.84 (m, 2H), 7.47-6.99 (m, 71), 4.75 (q, 3=6.9 Hz, 1H), 2.49 (s, 3H), 1.46 (d, J=6.9 Hz, 3H) ppm.

Provenance & Evidence