Toluene → 4-Methoxy-N-(4-methoxyphenyl)-N-phenylaniline

Participants

Reaction Steps

In a procedure modified from Thayumanavan et al. (Chem Mater., 1997, 9, 3231-3235), to a solution of 4.975 g (5.43 mmol) of tris(dibenzylideneacetone)-dipalladium (0) and 4.519 g (8.15 mmol) of 1,1′-bis(diphenylphosphino)-ferrocene in 680 mL toluene under nitrogen was added 68.46 mL (0.245 mol) of 4-bromoanisole and was allowed to stir for 25 minutes. Then, sodium t-butoxide (59.36 g, 0.618 mol) and aniline (22.5 mL, 0.236 mol) were added to the solution and stirred at 90° C. for approximately 2 weeks. The complete formation of decoupled product was monitored by thin layer chromatography. The reaction solution was then worked up with several (3×) brine washings, extracted with ether, and dried over MgSO4. A flash column of 5% ethyl acetate/95% hexanes gave a light brown solid. The still crude product was purified on a column with 1% ethyl acetate/99% hexanes mobile phase to afford 20.39 g of white solid. 1H NMR (CDCl3): δ3.98 (s, 6H), δ7.01-7.23 (m, 11H), δ7.36 (d, 2H); m/z 305.1 (M+), 290.1 (M+-CH3).

Provenance & Evidence