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ChemicalBook CAS DataBase List 2-Fluoro-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)benzonitrile
870238-67-8

2-Fluoro-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)benzonitrile synthesis

3synthesis methods
-

Yield:870238-67-8 89%

Reaction Conditions:

with palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride;anhydrous potassium acetate in 1,4-dioxane;dimethyl sulfoxide at 105; for 3 h;Inert atmosphere;

Steps:

xiv.a 2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile I37

A mixture of 4-bromo-2-fluorobenzonitrile (1.0 g, 5.0 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (1.3 g, 5.0 mmol), potassium acetate (5.9 g, 20.0 mmol) and Pd(dppf)Cl2 (2.0 g, 1.0 mmol) in DMSO (50 ml.) and 1,4-dioxane (10 ml.) was heated at 105 °C under N2 for 3 h. [82] The mixture was diluted with EtOAc (200 ml.) and washed with water (100 ml. x 3). The organic layer was dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure and the residue was purified by column chromatography (Pet. ether/EtOAc= 100/0 to 50/1) to give the title compound (1.1 g, 89%) as a white solid, which was used directly in the next step.

References:

WO2019/243491,2019,A1 Location in patent:Page/Page column 81-82