1-Bromo-4-tert-butylbenzene → HCID 57589730, compound

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Reaction Steps

To a flask equipped with a magnetic stirrer, reflux condensor, and nitrogen inlet was added 1,4-benzodioxin-6-amine (5.26 grams, 34.8 mmoles), 4-tert-butyl bromobenzene (6.83 grams, 32.1 mmoles), tris(dibenzylideneacetone)dipalladium (0) (0.58 grams, 0.6 mmoles), rac-2,2′-bis(diphenylphosphino)-1,1′-binapthyl (0.79 grams, 1.2 mmoles), sodium tert-butoxide (6.08 grams, 63.0 mmoles) and anhydrous toluene (70 mL). The contents of the flask were refluxed for three days; cooled to room temperature; and filtered through a pad of silica gel. The silica gel pad was then eluted with dichloromethane (300 mL). The combined organic layers were concentrated in vacuo to yield a dark solid. The solid was chromatographed on silica gel, eluting with a hexane/ethyl acetate gradient to afford 5 grams of the desired product as a white solid. 1H NMR (CDCl3) δ 7.25 (d, 2H), 6.9 (d, 2H), 6.75 (d, 1H), 6.5-6.7 (m, 2H), 5.4 (bs, 1H), 4.2 (s, 4H), 1.3 (s, 9H).

Provenance & Evidence