4-CHLORO-3-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER synthesis
- Product Name:4-CHLORO-3-TRIFLUOROMETHYLPHENYLBORONIC ACID, PINACOL ESTER
- CAS Number:445303-09-3
- Molecular formula:C13H15BClF3O2
- Molecular Weight:306.52
445-01-2
235 suppliers
$13.00/25g
73183-34-3
578 suppliers
$6.00/5g
445303-09-3
50 suppliers
$55.00/250mg
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