Nitrogen → HCID 22905873, compound

Participants

Reaction Steps

A cold solution of 1,5-dibromo-2-(2-bromoethoxy)-3-tert-butylbenzene (5.00 g, 12.05 mmol) in tetrahydrofuran/hexane (100 mL/20 mL) is cooled to -95° C. (MeOH/Et2O, liquid N2). A solution of n-butyl lithium in hexane (12 mL, 30.1 mmol) is added dropwise, and the reaction is allowed to stir for 0.5 h between -95° C. and -80° C. After 4 h, the reaction is poured onto saturated NH4Cl, and extracted with ethylacetate. The organic layer is washed twice with H2O and once with brine. The combined organic layers are dried (MgSO4), filtered, and evaporated. The resulting oil is purified by chromatography over SiO2 using hexanes. The resulting oil is distilled at reduced pressure to give 7-tert-butyl-2,3-dihydrobenzo[b]furan as a low melting white solid.

Provenance & Evidence