Potassium Carbonate → 1443377-33-0

Participants

Reaction Conditions

Reaction Steps

A solution of PdCl2(dppf)-CH2Cl2 adduct (1.391 g, 1.703 mmol), cyclopropylboronic acid (4.39 g, 51.1 mmol), 1-bromo-4-iodo-2-methoxybenzene (10.66 g, 34.1 mmol), and potassium carbonate (18.83 g, 136 mmol) in 100 mL dioxane/50 mL water was heated to 120° C. for 8 hours. LC/MS showed mostly product, so the reaction mixture was diluted with heptane and was washed with saturated NaHCO3 solution. The organics were dried over MgSO4 and concentrated. The crude residue was taken up in 100 mL dioxane, was treated with Pd2(dba)3 (0.399 g, 1.703 mmol), dicyclohexyl(2′,4′,6′-triisopropyl-[1,1′-biphenyl]-2-yl)phosphine (4.06 g, 8.52 mmol), bis(pinacolato)diboron (12.98 g, 51.1 mmol), and potassium phosphate (28.9 g, 136 mmol) and was heated to 120° C. overnight. LC/MS showed product, so the reaction mixture was diluted with heptane then filtered through a plug of diatomaceous earth. The filtrate was concentrated then purified directly by silica gel column chromatography (0-25% EtOAc/heptane) yielding 2-(4-cyclopropyl-2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.68 g, 9.78 mmol, 28.7% yield). m/z (ESI) 297.3 (M+Na)+

Provenance & Evidence