反应详情

温度

80 °C

To a flask equipped with a magnetic stirrer, reflux condensor, and nitrogen inlet was added N,N-diethyl-1,4-phenylenediamine (3.35 grams, 20.4 mmoles), 5-bromo-2,3-dihydrobenzofuran (3.4 grams, 17.1 mmoles), tris(dibenzylideneacetone)dipalladium (0) (0.39 grams, 0.43 mmoles), rac-2,2′-bis(diphenylphosphino)-1,1′-binapthyl (2.1 grams, 3.4 mmoles), sodium tert-butoxide (0.71 grams, 1.28 mmoles) and anhydrous toluene (90 mL). The contents of the flask were heated to 80° C. for two days; cooled to room temperature; and filtered through a pad of silica gel. The silica gel pad was then eluted with dichloromethane (200 mL). The combined organic layers were concentrated in vacuo to yield a dark blue oil. The oil was chromatographed on silica gel, eluting with a hexane/ethyl acetate gradient to afford 4.2 grams of the desired product as a brown oil. 1H NMR (CDCl3) δ 6.6-7.0 (m, 7H), 5.15 (bs, 1H), 4.5 (t, 2H), 3.05-3.2 (m, 6H), 1.1 (t, 6H).

1. customTo a flask equipped with a magnetic stirrer
2. temperaturereflux condensor, and nitrogen inlet
3. temperaturecooled to room temperature
4. filtrationand filtered through a pad of silica gel
5. washThe silica gel pad was then eluted with dichloromethane (200 mL)
6. concentrationThe combined organic layers were concentrated in vacuo
7. customto yield a dark blue oil
8. customThe oil was chromatographed on silica gel
9. washeluting with a hexane/ethyl acetate gradient