ChemicalBook CAS DataBase List Methyl 2-(2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate

Methyl 2-(2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate synthesis

8synthesis methods

Product Name:Methyl 2-(2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate
CAS Number:849934-95-8
Molecular formula:C15H20BClO4
Molecular Weight:310.58

849934-94-7 Synthesis

Methyl 2-(4-broMo-2-chlorophenyl)acetate

849934-94-7
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73183-34-3
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Methyl 2-(2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate

849934-95-8
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Yield:849934-95-8 99%

Reaction Conditions:

with dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct;anhydrous potassium acetate in 1,4-dioxane; for 18 h;Inert atmosphere;Reflux;

Steps:

Methyl-2-(2-chloro-4-(1,1,2,2-tetramethyl-1λ4,2λ4,4-dioxaborolan-4-yl)phenyl)acetate (4)

In a flame-dried flask under inert atmosphere, 3 (18.3 g, 70.0 mmol, 1.0 equiv.), was diluted in 1,4-dioxane (278 mL) then bis(pinacolato)diboron (23.0 g, 90.5 mmol, 1.3 equiv.), KOAc (20.5 g, 209 mmol, 3.0 equiv.), and Pd(dppf)Cl2-DCM (2.8 g, 3.5 mmol, 0.05 equiv.) were all added. The mixture was heated at reflux for 18 h, reduced, dissolved in EtOAc, passed through a plug of silica gel, and then reduced to yield the white solid 4 (22.0 g, >99 %). Characterization data was identical to previous reports.[21]

References:

Koval, Alexander B.;Wuest, William M. [Tetrahedron Letters,2016,vol. 57,# 3,p. 449 - 451] Location in patent:supporting information

849934-94-7 Synthesis

849934-94-7
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96042-30-7 Synthesis