3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol synthesis

Yield:-

Reaction Conditions:

with triethylamine;PdCl₂(PPh₃)2 in 1,4-dioxane;

Steps:

224.a a

a 3,5-Dimethyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol Following the procedure described in Example 220, step a, reaction of 4-bromo-3,5-dimethyl-phenol (1.5 gm, 7.6 mmol), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.3 mL, 23 mmol, Aldrich Chemical Company), PdCl₂(PPh₃)₂ (530 mg, 0.76 mmol, Strem Chemicals Inc, Newburyport, Mass.), Et₃N (634 μL, 46 mmol), and dioxane (30 mL) afforded 3.4 gm of a tan glassy solid after chromatography (50 gm, silica SPE column) which was used without further purification. ¹H-NMR (CDCl₃; 400 MHz): δ 6.4 (s, 2H), 2.3 (s, 6H), 1.4 (s, 12H).

References:

US2004/9995,2004,A1