Methane → HCID 57671288, compound

Participants

Reaction Steps

Alternate Step 2) Stir a slurry of 2-(3,5-dichloro-4-methyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (300 g, 1.05 moles) in 2 L of isopropanol under a blanket of nitrogen. Add p-bromofluorobenzene 61619 (150 mL; 1.36 moles) followed by an aqueous solution of potassium carbonate (160.5 g; 1.15 moles) in 300 mL water. Rinse the addition funnel with 400 mL isopropanol. Add triphenylphosphine (12.3 g; 46.89 mmoles) and Pd(OAc)2 (2.35 g; 10.47 mmoles) and heat the mixture at 75° C. for 8 h. Add water (300 mL) and allow the mixture to cool to room temperature to afford a slurry. Cool the slurry in an ice bath, collect the solid by filtration and rinse with 350 mL of 6:1 IPA-water. Dry the solid in a vacuum oven at room temperature overnight to afford 345 g of crude product. Suspend the crude product in 2.2 L of ethanol and heat at 70° C. to afford a solution. Add Darco (35 g) and stir for 30 min. Filter the mixture through a pad of Hyflo (Celite) and allow the solution to cool to room temperature to afford a slurry. Cool the slurry to 5° C., collect the solid by filtration, and rinse with cold ethanol (530 mL). Dry the solid under vacuum to afford 230 g of 3,5-dichloro-4′-fluoro-4-methyl-biphenyl as an off-white solid (86% yield).

Provenance & Evidence