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ChemicalBook CAS DataBase List 4-CHLORO-3-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER
445303-09-3

4-CHLORO-3-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER synthesis

1synthesis methods
-

Yield:445303-09-3 66%

Reaction Conditions:

with potassium acetate;PdCl2(PPh3)2 in 1,4-dioxane;ethyl acetate;

Steps:

2-(4-chloro-3-trifluoromethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

2-(4-chloro-3-trifluoromethyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane This compound was prepared in a modification of the literature known method (Y. Masuda, M. Murata, S. Watanabe, J. Org. Chem., 1997, 62, 6458-9). To a flask containing KOAc (3.4 g, 34.7 mmol), PdCl2(PPh3)2 (234 mg, 0.34 mmol) and bis(pinacolato)diboron (3.2 g, 12.7 mmol) was added a solution of 5-bromo-2-chloro-benzotrifluoride (3 g, 11.5 mmol) in dioxane. This mixture was heated to 100° C. under an argon atmosphere for 3 h. After cooling, AcOEt was added then the organic mixture was washed with saturated NaCl solution then dried with Na2SO4 and the solvent evaporated. The residue was chromatographed (silica, elution with hexane/AcOEt=9:1) to afford the title compound (2.35g, 66%) as a light brown solid. MS: m/e=306.1 (M+).

References:

US2002/151715,2002,A1

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