4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)FLUOROBENZENE Chemical Properties

Boiling point:

279.4±23.0 °C(Predicted)

Density 

1.05±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to lump to clear liquid

color 

White or Colorless to Light yellow to Light orange

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2931900090

4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)FLUOROBENZENE Usage And Synthesis

Synthesis

General steps: 1. Stirring reaction: potassium acetate (KOAc, 0.073 g, 0.09 mmol) and 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride-dichloromethane complex (PdCl2(dppf)-CH2Cl2, 0.613 g, 3.5 mmol) were added under argon protection to a mixture of potassium acetate (1b, R = F 0.613 g, 3.5 mmol) and bis(pinacolato)diboron (2, 1.161 g, 4.5 mmol) in a solution of dimethyl sulfoxide (DMSO, 1.601 g). The reaction mixture was stirred at 80°C for 1.5 hours. 2. Extraction: Upon completion of the reaction, the reaction solution was cooled to room temperature, the reaction was quenched by the addition of ice water, followed by extraction of the organic layer with ethyl acetate (EtOAc, 80 mL × 2). 3. Drying and concentration: The organic layers were combined, dried with anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure to obtain the crude product. 4. Purification: The crude product was purified by column chromatography (silica gel, eluent: hexane/EtOAc = 9:1) to afford 4-fluorophenylboronic acid pinacol ester (3b, R = F) in 93% yield.

References

[1] Patent: JP5966165, 2016, B2. Location in patent: Paragraph 0056-0062
[2] Journal of the American Chemical Society, 2016, vol. 138, # 9, p. 2985 - 2988
[3] Advanced Synthesis and Catalysis, 2016, vol. 358, # 6, p. 977 - 983
[4] Journal of Fluorine Chemistry, 2015, vol. 178, p. 195 - 201
[5] ACS Catalysis, 2018, vol. 8, # 5, p. 4049 - 4054

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