P-Anisidine → 4-(3-(tert-butyldimethylsilyloxy)propoxy)-N-(4-methoxyphenyl)aniline

Participants

Reaction Conditions

Reaction Steps

5. To a dry 500 mL round bottom flask under nitrogen was added (3-(4-bromophenoxy)propoxy)(tert-butyl)dimethylsilane (12.1 g, 35.0 mmol), 4-anisidine (5.17 g, 42.0 mmol), and 20 mL anhydrous toluene. The mixture was degassed for 10 minutes before addition of dibenzylideneacetone di palladium Pd2(dba)3 (0.64 g, 0.70 mmol), 1,1′-Bis(diphenylphosphino)ferrocene (DPPF) (0.68 g, 1.2 mmol), and 20 mL anhydrous toluene. After 10 minutes of mixing, sodium tert-butoxide (4.7 g, 49.0 mmol) was added with 10 mL anhydrous toluene. The reaction mixture was heated to 90° C. and allowed to stir overnight while being monitored by thin layer chromatography. Upon disappearance of the starting material the reaction mixture was filtered through a plug of silica gel eluting with dichloromethane (Reaction Time=22 h). The product was purified by flash chromatography (silica gel, 5:1 hexanes:ethyl acetate). The solvent was removed under reduced pressure. The residual solvent was removed in vacuo (11.3 g, 83.0%). 1H NMR (300 MHz, CDCl3) δ 7.06 (d, J=3.3 Hz, 2H), 7.03 (d, J=3.3 Hz, 2H), 6.91 (d, J=3.3 Hz, 2H), 6.88 (d, J=3.3 Hz, 2H), 6.85 (s, 1H), 4.10 (t, 6.3 Hz, 2H), 3.90 (t, J=6.0 Hz, 2H), 3.81 (s, 3H), 2.01 (q, J=6.3 Hz, 2H), 0.97 (s, 9H), 0.14 (s, 6H).

Provenance & Evidence