1-Bromo-4-fluorobenzene → HCID 57671288, compound

Participants

Reaction Conditions

Reaction Steps

Step 2) To a suspension of 2-(3,5-Dichloro-4-methyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (119 g; 414.64 mmoles) in 1,2-dimethoxyethane (240 mL) under nitrogen, add p-bromofluorobenzene (57 mL; 518.54 mmoles), water (120 mL), potassium carbonate (115.7 g; 828.79 mmoles), triphenylphosphine (2.72 g; 10.37 mmoles) and Pd(OAc)2 (0.47 g; 2.09 mmoles). Heat the mixture at 80° C. for 12 h and then allow to cool to room temperature. To the mixture, add 240 mL of t-butyl methyl ether and 480 mL of water, and then separate the layers. Wash the organic layer with an aqueous solution of TMT (Trithiocyanuric acid, trisodium salt hydrate, 5 g) in 120 mL, followed by saturated aqueous NaCl (120 mL). Solvent exchange the organic layer into approximately 600 mL of isopropanol to afford a slurry. Add water (120 mL) and cool the slurry to 3° C. Collect the solid by filtration and wash with 120 mL of cold methanol. Dry the solid under vacuum to afford 92.8 g of 3,5-dichloro-4′-fluoro-4-methyl-biphenyl as a light yellow solid. 1H NMR (CDCl3, 500 MHz) δ 2.49 (3H, s), 7.13 (2H, t, J=9 Hz), 7.46 (2H, s), 7.49 (2H, dd, J=9, 5 Hz).

Provenance & Evidence