Sodium Carbonate → 7-(3,5-Dimethylphenyl)-2-methyl-1-indanone

Participants

Reaction Conditions

Reaction Steps

Using a method similar to Example 16b), 16.25 g (0.09 mol) of (1), 14.85 g (0.1 mol) of 3,5-dimethylphenylboronic acid, 21.2 g (0.2 mol) of sodium carbonate were placed in 240 ml of o-xylene/80 ml of water in the reaction vessel, the mixture was degassed a number of times and saturated with argon. After addition of 101 mg (0.45 mmol) of palladium acetate and 472 mg (1.8 mmol) of TPP, the reaction mixture was stirred for 8 hours at 100° C. After 2, 4 and 6 hours, the same amounts of palladium acetate and triphenylphosphine were added again each time. After addition of 150 ml of water, the phases were separated, the aqueous phase was extracted 3 times with 200 ml each time of ether, the combined organic phases were washed with 200 ml of water and 200 ml of saturated sodium chloride solution and dried over magnesium sulfate. Removal of the solvent gave 20.3 g of (17) as an oil.

Provenance & Evidence