1-Bromo-3,4-(methylenedioxy)benzene → HCID 58980587, compound

Participants

Reaction Conditions

Reaction Steps

To a flask equipped with a magnetic stirrer, reflux condensor, and nitrogen inlet was added 3,4-(methylenedioxy) aniline (5.34 grams, 38.9 mmoles), 4-bromo-1,2-(methylenedioxy) benzene (6.41 grams, 31.9 mmoles), tris(dibenzylideneacetone)dipalladium (0) (0.71 grams, 0.8 mmoles), 1,1′-bis(diphenylphosphino)-ferrocene (1.29 grams, 2.3 mmoles), sodium tert-butoxide (4.20 grams, 43.7 mmoles) and anhydrous toluene (40 mL). The contents of the flask were heated to 80° C. for three days; cooled to room temperature; and filtered through a pad of silica gel. The silica gel pad was then eluted with dichloromethane (240 mL). The combined organic layers were concentrated in vacuo to yield a dark yellow oil. The oil was chromatographed on silica gel, eluting with a hexane/ethyl acetate gradient to afford 6 grams of yellow solid. The solid was triturated with hexane and filtered to afford 3.9 grams of the desired product as a white solid. 1H NMR (CDCl3) δ 6.7 (d, 2H), 6.55 (s, 2H), 6.35 (d, 2H), 5.85 (s, 4H), 5.35 (bs, 1H).

Provenance & Evidence