P-Anisidine → 5-Bromo-7-t-butyl-3,3,6-trimethyl-2,3-dihydro-benzofuran

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-7-isopropyl-3,3,6-trimethyl-2,3-dihydro-benzofuran (Compound 50, 0.56 g, 1.98 mmol), p-anisidine (0.48 g, 3.96 mmol), sodium tert-butoxide (0.27 g, 2.77 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.020 g, 0.02 1 mmol) and (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.040 g, 0.064 mmol) in 6 mL of anhydrous toluene was heated at 80° C. under argon overnight. The reaction mixture was cooled to ambient temperature, diluted with diethylether and filtered. The filtrate was evaporated in vacuo to a residue which on flash column chromatography using 10% ethyl acetate in hexane as the eluent afforded the title compound (0.6 g, 93%) as a pink solid. 1H NMR (300 MHz, CDCl3): δ 6.76 (d, 2H, J=8.9 Hz), 6.75 (s, 1H), 6.61 (d, 2H, J=8.9 Hz), 5.0 (s, 1H), 4.15 (s, 2H), 3.71 (s, 3H), 3.24 (heptet, 1H, J=7.0 Hz), 2.17 (s, 3H), 1.33 (d, 6H, J=7.0 Hz), 1.25 (s, 6H).

Provenance & Evidence