4-Isopropylaniline → HCID 86620567, compound

Participants

Reaction Steps

In the drybox, a 500 mL one-neck round-bottom flask was charged with dibromochrysene (9 g, 23.3 mmol), 4-iso-propylaniline (6.61 g, 48.9 mmol) and 200 mL of dry toluene. In a separate 100 ml flask, Pd2(dba)3 (0.192 g, 0.21 mmol), P(t-Bu)3 (0.085 g, 0.42 mmol) were dissolved in 25 ml of dry toluene, stirred for 10 minutes and then added to the dibromochrysene/aniline solution. After ten minutes of stirring, sodium tert-butoxide (4.48 g, 46.6 mmol) was added in one portion. The reaction flask was brought out of the drybox, capped with a nitrogen inlet and stirred in an 80° C. oil bath overnight (18 h). Next day, reaction mixture was cooled to room temperature, poured onto 15 g of silica gel and 15 g of celite, swirled around for a few minutes and filtered through a 4 inch plug of silica gel, washing with 5.5 liters of toluene. Volatiles were removed under vacuum to give a dark yellow solid. The solid was triturated with diethyl ether, vacuum filtered and washed with minimal amount of ether. The resulting yellow solid was dried on a high vacuum line. Yield 8.68 g (75.5%). The compound was confirmed by NMR analysis.

Provenance & Evidence