2-(4-Cyclohexylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical Properties

Boiling point:

387.1±21.0 °C(Predicted)

Density 

1.00±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

Safety Information

HS Code 

2931900090

2-(4-Cyclohexylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Usage And Synthesis

Synthesis

Under nitrogen protection, 0.382 g of bis(pinacolato)diboron (1.2 eq.), 27.5 mg of dichloro[[1,1 '-bis(diphenylphosphino)ferrocene]palladium(II) (0.03 eq.), 41.7 mg of [1,1 '-bis(diphenylphosphino)ferrocene] (0.06 eq.), and 0.369 g of potassium acetate (3 eq.) were sequentially added to a solution containing 0.3 g of 1-bromo-4-cyclohexylbenzene to a 5 mL solution of degassed 1,4-dioxane. The reaction mixture was stirred at 80 °C for 17 hours. After completion of the reaction, the reaction solution was diluted with 100 mL of ethyl acetate, washed three times sequentially with 60 mL of water, the organic phase was dried with anhydrous sodium sulfate, and the solvent was removed by concentration under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: 95/5 heptane/ethyl acetate) to give 0.2 g 4-cyclohexylphenylboronic acid pinacol ester in 56% yield.1H NMR (DMSO) δ (ppm): 7.60 (d, 2H), 7.20 (d, 2H), 1.70 (m, 5H), 1.40 (m, 4H), 1.30 (m, 12H) .

References

[1] Patent: WO2005/3115, 2005, A1. Location in patent: Page/Page column 28

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