Cesium fluoride → 8-(2,5-Dimethyl-4-nitrophenyl)-1,4-dioxaspiro[4.5]dec-7-ene

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-bromo-2,5-dimethyl-4-nitrobenzene (100 mg, 0.43 mmol), 4,4,5,5-tetramethyl-2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-1,3,2-dioxaborolane (112 mg, 0.43 mmol), Pd(PPh3)4 (49 mg, 0.043 mmol) and CsF (196 mg, 1.29 mmol) in a mixture of dimethyl ethylene glycol and water (2:1, 1.5 mL) was degassed and heated under N2 at 130° C. in microwave reactor for 15 min. After cooling down to room temperature, the reaction mixture was treated with saturated NH4Cl aqueous solution (5 mL) and extracted with EtOAc (3×4 mL). The combined organic layers were concentrated and purified by flash column chromatography (silica gel, 0%-30% EtOAc in hexanes gradient) to provide 8-(2,5-dimethyl-4-nitrophenyl)-1,4-dioxaspiro[4.5]dec-7-ene as a white solid; ESMS m/z 290.1 (M+H+).

Provenance & Evidence