P-Anisidine → 7-t-Butyl-5-[(4-methoxy-phenyl)-amino]-3,3,6-trimethyl-2,3-dihydro-benzofuran

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Reaction Steps

Following general procedure K and using 5-bromo-7-t-butyl-3,3,6-trimethyl-2,3-dihydro-benzofuran (Compound 51, 0.33 g, 1.1 mmol), p-anisidine (0.25 g, 2 mmol), sodium tert-butoxide (0.2 g, 2.1 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.030 g, 0.03 mmol) and (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.060 g, 0.096 mmol) in 3 mL of anhydrous toluene, the title compound (0.37 g, quantitative yield) was obtained as a pink solid. 1H NMR (300 MHz, C6D6): δ 6.79 (d, 2H, J=8.9 Hz), 6.72 (s, 1H), 6.60 (d, 2H, J=8.7 Hz), 4.60 (br s, 1H), 3.90 (s, 2H), 3.35 (s, 3H), 2.37 (s, 3H), 1.68(s, 9H), 1.02 (s, 6H).

Provenance & Evidence