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

Participants

Reaction Steps

The synthesis of the triphenylamine donor Wittig salt follows the schematic in FIG. 9. 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(diphenylphosphine)-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 tert-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. Thin layer chromatography was used to monitor the complete formation of the decoupled product. The reaction solution was then worked up with brine washings (3×), 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 give 21.19 g of white solid. 1H NMR (CDCl3): δ3.87 (s, 6H), δ6.87-7.08 (m, 11H), δ7.26 (d, 2H).

Provenance & Evidence