Sodium Carbonate → HCID 86723235, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(2-methoxy-4-(methylsulfonyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Preparation 16, 3.04 g, 9.74 mmol), 5-bromo-2-fluoro-iodobenzene (2.66 g, 8.85 mmol), and Na2CO3 (2.80, 26.55 mmol) in dioxane (60 mL) and water (15 mL) was degassed, tetrakis(triphenylphosphine)palladium(0) was added and the reaction mixture was degassed again. The reaction mixture was heated at 110° C. for 3 hours before cooling to room temperature and concentrating under reduced pressure. The residue was partitioned between water (100 mL) and EtOAc (100 mL). The organic phase was separated and the aqueous layer was re-extracted with EtOAc (2×100 mL). The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure to give the crude. The crude was purified by silica gel column chromatography eluting with 10-30% EtOAc/heptane to afford the title compound in 71% yield, 2.25 g.

Provenance & Evidence