Benz[f]indene (10.8 g, 0.065 mole) was dissolved in 100 mL of dimethylformamide. 1-Bromo-3,5-di-t-butylbenzene (14 g, 0.052 mole) was added along with palladium acetate (0.3 g), tri-o-tolylphosphine (0.8 g), and triethyl amine (11.0 g). The solution was heated to 60° C. for 3 days. The solution was cooled and washed with 1 N HCl and by saturated sodium bicarbonate. The product was found to be difficult to separate from the residual tri-o-tolylphosphine. After purifying by passing through silica with hexanes three times, and recrystallization from ethanol, followed by three recrystallizations from hexanes, it yielded 5.8 g of 2-(3,5-di-t-butylphenyl)benz[f]indene (26% yield). 1HNMR (CDCl3, 300 MHz δ7.95-7.77 (m, 4H); 7.52-7.37 (m, 5H); 7.23 (s, 1H); 3.99 (s, 2H); 1.43 (s, 18H).
