4-Difluoromethoxyphenylboronic acid pinacol ester Chemical Properties

Boiling point:

319.3±37.0 °C(Predicted)

Density 

1.13±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

Appearance

Light yellow to light brown Solid

InChI

InChI=1S/C13H17BF2O3/c1-12(2)13(3,4)19-14(18-12)9-5-7-10(8-6-9)17-11(15)16/h5-8,11H,1-4H3

InChIKey

BPFSJXBWEVRJFH-UHFFFAOYSA-N

SMILES

O1C(C)(C)C(C)(C)OB1C1=CC=C(OC(F)F)C=C1

Safety Information

HS Code 

2931900090

4-Difluoromethoxyphenylboronic acid pinacol ester Usage And Synthesis

Synthesis

A. General procedure for the synthesis of 2-(4-(difluoromethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane: Under nitrogen protection, 1-bromo-4-(difluoromethoxy)benzene (1 g, 4.48 mmol), pinacol ester of bis(boronic acid) (1.2 g, 4.71 mmol), potassium acetate (1.3 g, 13.4 mmol), and PdCl2(dppf)-CH2Cl2 adduct (0.18 g, 0.22 mmol) were dissolved in DMF (15 mL) at 90 °C for 1 h. The reaction was stirred. After completion of the reaction, the reaction mixture was diluted with dichloromethane, washed sequentially with water, saturated NaHCO3 solution and brine, and the organic phase was dried with anhydrous MgSO4 and concentrated. The crude product was purified by ISCO fast chromatography (silica gel column, eluent 100:0 to 50:50 hexane/ethyl acetate gradient) to afford the target product 2-(4-(difluoromethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.12 g, 3.32 mmol, yield 74.0%) as a brown oil.

References

[1] Organic Process Research and Development, 2018, vol. 22, # 4, p. 557 - 561
[2] Patent: WO2010/104830, 2010, A1. Location in patent: Page/Page column 98-99
[3] Patent: US2012/329802, 2012, A1. Location in patent: Page/Page column 33
[4] Patent: US2007/60623, 2007, A1. Location in patent: Page/Page column 49
[5] Patent: WO2009/26276, 2009, A1. Location in patent: Page/Page column 49-50

4-Difluoromethoxyphenylboronic acid pinacol ester(887757-48-4)Related Product Information

• Boronic acid, [4-(difluoromethoxy)phenyl]- (9CI)
• 4,4,5,5-TETRAMETHYL-2-(4-TRIFLUOROMETHOXYPHENYL)-1,3,2-DIOXABOROLANE
• 2-(2-(Bromomethyl)-4-(trifluoromethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 4-Difluoromethoxyphenylboronic acid pinacol ester