General procedure for the synthesis of 4-bromo-3-nitrophenylboronic acid from 2-bromo-5-fluoronitrobenzene and bis(pinacolato)diboronic acid: 2-bromo-5-fluoronitrobenzene (19.48 g, 89 mmol) was added to a 1L round bottom flask. Bis(pinacolato)diboron (27 g, 106 mmol), bis(triphenylphosphine)dichloropalladium (3.1 g, 4.45 mmol), and potassium acetate (KOAc) (22 g, 222 mmol) were added sequentially, followed by 1,4-dioxane (445 mL). The mixture was heated to reflux with stirring. After 3 hours of reaction, the heating was stopped and the mixture was cooled to room temperature. The separation was carried out by extraction with dichloromethane and distilled water. The organic layer was dried and purified by column chromatography to afford the intermediate 4-bromo-3-nitrophenylboronic acid (13.08 g, 60% yield).
