ChemicalBook CAS DataBase List (naphthalene-1-yl)-{4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-

(naphthalene-1-yl)-{4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2- synthesis

4synthesis methods

Product Name:(naphthalene-1-yl)-{4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-
CAS Number:528610-01-7
Molecular formula:C28H28BNO2
Molecular Weight:421.34

73183-34-3
591 suppliers
$6.00/5g

138310-84-6
108 suppliers
$27.00/200mg

(naphthalene-1-yl)-{4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-

528610-01-7
22 suppliers
inquiry

Yield:528610-01-7 97%

Reaction Conditions:

with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;potassium acetate in toluene at 100;Inert atmosphere;

Steps:

1 N-phenyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)naphthalen-1-amine (Compound 5)

Compound 5 [Shin, D.; Paek, W.; Choi, B.; Kwon, O.; Kim, M.; Son, Y.; Han, E.; Song, J. U.S. Pat. Appl. Publ., 20070276160, 29 Nov. 2007] was prepared as follows: a mixture of Compound 4 (2.54 g, 6.79 mmol), bis(pinacolato)diboron (3.62 g, 14.3 mmol), [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II) (0.298 g, 0.407 mmol), potassium acetate (2.00 g, 20.4 mmol) and anhydrous toluene (50 mL) was degassed with argon for about 28 min while stirring. The reaction mixture was then maintained under argon at about 100° C. while stirring. Upon confirming consumption of the starting material by TLC (SiO₂, 4:1 hexanes-CH₂Cl₂), the reaction was cooled to RT and poured over EtOAc (ca. 200 mL). The organics were then washed with sat. NaHCO₃, water and brine, dried over MgSO₄, filtered and concentrated in vacuo. Purification of the crude product via flash chromatography (SiO₂, 2:1 to 3:2-hexanes: CH₂Cl₂to 100% CH₂Cl₂) yielded Compound 5 (2.78 g, 97%) as a colorless foam: confirmed by LCMS (APCI): calculated for C₂₈H₂₉BNO₂(M+H⁺): 422; Found: 422.