3-Chloro-4-hydroxyphenylboronic acid Chemical Properties

Melting point:

223-228°C

Boiling point:

360-361°

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

color 

White to Light yellow to Light red

CAS DataBase Reference

182344-13-4

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT, KEEP COLD

HS Code 

2931900090

3-Chloro-4-hydroxyphenylboronic acid Usage And Synthesis

Uses

suzuki reaction

Synthesis

General procedure for the synthesis of 3-chloro-4-hydroxyphenylboronic acid from 4-bromo-2-chlorophenol: 1. n-BuLi (12 mL of 2.44 M solution, 29 mmol) was added slowly and dropwise to a stirring solution of 4-bromo-2-chlorophenol (5 g, 24 mmol) in anhydrous THF (75 mL) at -78°C and stirring was continued for 2 hours at -78°C. 2. trimethyl borate (3.3 mL, 29 mmol) was added to the reaction mixture, followed by allowing the reaction mixture to slowly warm to room temperature and stirring for 19 hours. 3. The reaction was quenched using 2M HCl aqueous solution followed by organic phase extraction with EtOAc (2 x 60mL). 4. The organic extracts were combined and concentrated under reduced pressure to give an oily substance containing a white precipitate. 5. Hexane was added to the oily substance, and the white powder was collected by filtration and washed with hexane. Yield: 15%. 1H NMR (270 MHz, DMSO-d6) δ: 6.49 (bs), 6.91 (1H, d, J = 7.9 Hz), 7.54 (1H, dd, J = 8.2, 1.5 Hz), 7.72 (1H, d, J = 1.5 Hz), 8.02 (bs), 10.32 (1H, s). HPLC retention time: 3.36 min (>91% purity, aqueous solution of 90% MeCN). LC/MS (APCI) m/z: 171.16 (M-H)-.

References

[1] Patent: WO2007/96647, 2007, A2. Location in patent: Page/Page column 125-126
[2] Patent: WO2007/68905, 2007, A1. Location in patent: Page/Page column 120-121; 148-149; 152-153; 154-155
[3] Journal of the American Chemical Society, 2007, vol. 129, # 7, p. 1894 - 1895

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