1,1'-Biphenyl, 2-methyl-3-nitro-3'-(trifluoromethoxy)- synthesis

Yield:957211-49-3 96%

Reaction Conditions:

with potassium carbonate;bis-triphenylphosphine-palladium(II) chloride in 1,4-dioxane at 100; for 3 h;

Steps:

1.A

A mixture of 2-bromo-6-nitrotoluene (21.5 g, 99.5 mmol), 3-trifluoromethoxylbenzeneboronic acid (27.0 g, 131.1 mmol), Pd(PPh₃)₂Cl₂ (3.50 g, 5.0 mmol) and 2M K₂CO₃ (120 mL, 240 mmol) in dioxane (330 mL) was degassed with N₂ and then heated at 100° C. for 3 h. After cooling to room temperature, the reaction mixture was passed through Celite and partitioned between EtOAc and H₂O. The combined organic phases were dried (MgSO₄), concentrated and purified by column chromatography (1-10% EtOAc/Heaxane) to give A15 (28.27 g, 96%) as light yellow oil: ¹H NMR (300 MHz, CDCl₃) δ 7.85 (d, J=7.82 Hz, 1 H), 7.74-7.38 (m, 3 H), 7.31-7.23 (m, 2 H), 7.19 (s, 1 H), 2.37 (s, 3H).

References:

US2007/265304,2007,A1 Location in patent:Page/Page column 26; 30