Sodium Carbonate → HCID 66743556, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 8-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,4-dioxa-spiro[4.5]dec-7-ene (as prepared by PCT Int. Appl. WO2006064189, 1.81 g, 6.80 mmol), 4-bromo-phenyl-acetonitrile (Aldrich, 1.40 g, 7.10 mmol), and tetrakis(triphenylphosphino)-palladium(0) (Aldrich, 350 mg, 0.34 mmol) in 1,4-dioxane (20 mL), was treated with 2M aqueous Na2CO3 (7 mL, 14.0 mmol), bubbled with argon for a few minutes, and heated to 100° C. under reflux condenser for 24 h. After cooling to ambient temperature, the reaction was diluted with water (30 mL) and extracted thrice with dichloromethane. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered, and the filtrate concentrated in vacuo to give a colorless oil. Purification by silica gel column, using a CombiFlash® system using hexanes and ethyl acetate as eluent (from pure hexanes to pure ethyl acetate), afforded the title compound as a white solid.

Provenance & Evidence