ChemicalBook CAS DataBase List tert-butyl Methyl(3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbaMate

tert-butyl Methyl(3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbaMate synthesis

4synthesis methods

Product Name:tert-butyl Methyl(3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbaMate
CAS Number:817618-57-8
Molecular formula:C18H28BNO4
Molecular Weight:333.23

57598-34-2 Synthesis

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tert-butyl Methyl(3-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbaMate

817618-57-8
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Yield:817618-57-8 98%

Reaction Conditions:

with potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in N,N-dimethyl-formamide at 80; for 6.25 h;

Steps:

4.c c-tert-Butyl methyl[3-(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)phenyl]carbamate:

c-tert-Butyl methyl[3-(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)phenyl]carbamate:10.1 g (102.6 mmol) of potassium acetate and 13.1 g (51.4 mmol) of bis-pinacoldiborane are added to a solution of 9.8 g (34.2 mmol) of tert-butyl (3-bromophenyl)-N-methylcarbamate in 300 mL of dimethylformamide. After bubbling nitrogen through the reaction mixture for 15 minutes, 1.1 g (1.4 mmol) of dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium are added. The reaction mixture is heated at 80° C. for 6 hours with vigorous stirring. After cooling, the reaction is worked up by addition of 300 mL of water and extraction with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution and then dried over magnesium sulfate. The solvents are evaporated off. The crude product obtained is purified by chromatography on a column of silica eluted with a 95/5 heptane/ethyl acetate mixture to give 11.2 g (98%) of tert-butyl methyl[3-(4,4,5,5-tetramethyl[1.3.2]dioxaborolan-2-yl)phenyl]carbamate in the form of a colorless oil that crystallizes.

References:

US2009/12129,2009,A1 Location in patent:Page/Page column 12