Sodium Carbonate → HCID 86723255, compound

Participants

Reaction Conditions

Reaction Steps

To a degassed, room temperature solution of 4-bromo-1-fluoro-2-iodobenzene (2.80 g, 9.30 mmol) and 4-(ethylsulphonyl)benzeneboronic acid (2.27 g, 10.6 mmol), in anhydrous 1,4-dioxane (120 mL) was added aqueous Na2CO3 solution (1M, 46.5 mL, 46.5 mmol) followed by the tetrakistriphenylphosphine palladium(0) (537 mg, 0.465 mmol). The slightly yellow solution was degassed 3 times by vacuum/nitrogen refill then was heated to 100° C. with stirring for 2 hours. The reaction mixture was cooled then suspended in CH2Cl2 (50 mL) and filtered through a pad of celite. The pad was rinsed well with CH2Cl2 (100 mL) and the filtrate was washed with water (2×50 mL) then dried over anhydrous MgSO4 (s), filtered and evaporated in vacuo to give crude product as a yellow oil. Purification by silica gel column chromatography eluting with heptane:EtOAc 1:1 afforded the title compound as a colourless oil in 84% yield, 2.696 g.

Provenance & Evidence