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

Melting point:

99.3-100.2 °C

Boiling point:

324.9±32.0 °C(Predicted)

Density 

1.15±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

8.39±0.35(Predicted)

Appearance

White to off-white Solid

CAS DataBase Reference

760990-08-7

Safety Information

HS Code 

2931900090

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

Uses

3-Fluoro-4-hydroxyphenylboronic acid, pinacol ester

Synthesis

4-Bromo-2-fluorophenol (1.9 g, 9.9 mmol), bis(pinacolato)diboron (2.9 g, 11.4 mmol), potassium acetate (3.90 g, 39.7 mmol), and DPPF (0.27 g, 0.49 mmol) were used as raw materials and dissolved in 32 mL 1,4-dioxane. Nitrogen was passed into the solution for 5 min to deoxidize. Subsequently, PdCl2(dppf)-DCM (0.4 g, 0.49 mmol) was added and the reaction mixture was stirred under reflux conditions for 4 hours. Upon completion of the reaction, the reaction solution was filtered through diatomaceous earth and purified by column chromatography to afford the target product 3-fluoro-4-hydroxyphenylboronic acid pinacol ester (2.2 g, 93% yield).1H NMR (CDCl3) δ 7.49 (2H, m), 6.98 (1H, t), 5.31 (1H, brs), 1.33 (12H, s).

References

[1] Patent: EP3239143, 2017, A2. Location in patent: Paragraph 0417
[2] Patent: US2010/324068, 2010, A1. Location in patent: Page/Page column 30
[3] Patent: WO2014/209034, 2014, A1. Location in patent: Paragraph 432; 433; 434
[4] Patent: CN105384638, 2016, A. Location in patent: Paragraph 0678; 0679; 0680; 0681
[5] Journal of Medicinal Chemistry, 2016, vol. 59, # 23, p. 10479 - 10497

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