3-Ethoxy-4-fluorobenzeneboronic acid Chemical Properties

Boiling point:

328.1±52.0 °C(Predicted)

Density 

1.22±0.1 g/cm3(Predicted)

storage temp. 

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

form 

powder to crystal

pka

8.23±0.10(Predicted)

color 

White to Almost white

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2931900090

3-Ethoxy-4-fluorobenzeneboronic acid Usage And Synthesis

Uses

suzuki reaction

Synthesis

General procedure for the synthesis of 3-ethoxy-4-fluorophenylboronic acid from 2-fluoro-5-bromophenethyl ether: n-butyllithium (n-BuLi, 1.6 M hexane solution, 14.3 mL, 22.8 mmol) was slowly added to a tetrahydrofuran (THF, 60 mL) solution of 2-fluoro-5-bromophenethyl ether (3.86 g, 17.6 mmol) at -78 °C. The reaction mixture was stirred continuously at -78 °C for 40 min, followed by the addition of trimethyl borate (3.63 mL, 33 mmol). The reaction system was slowly warmed from -78 °C to room temperature and stirring was continued for 4 hours. Upon completion of the reaction, the reaction was quenched with 1.0 N hydrochloric acid (40 mL) followed by extraction of the organic phase with ethyl acetate (EtOAc). The organic layer was washed with brine and dried with anhydrous sodium sulfate (Na2SO4). After removal of solvent by evaporation under reduced pressure, the crude product was purified by grinding with ethyl acetate/hexane (1:4) solvent mixture. After filtration, the target product 3-ethoxy-4-fluorophenylboronic acid (9B, 2.2 g, 69% yield) was obtained as a white solid. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 1.42 (t, J = 7.03 Hz, 3H), 4.11 (q, J = 7.03 Hz, 2H), 7.03 (dd, J = 11.42,8.35 Hz, 1H), 7.18-7.29 (m, 2H), 7.35 (d, J = 7.91 Hz, 1H).

References

[1] Patent: US2010/227894, 2010, A1. Location in patent: Page/Page column 29
[2] Patent: US2007/3539, 2007, A1. Location in patent: Page/Page column 69

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