4-Bromo-2,3-difluorophenol Chemical Properties

Melting point:

53.0 to 57.0 °C

Boiling point:

213.3±35.0 °C(Predicted)

Density 

1.858±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

7.16±0.23(Predicted)

form 

powder to crystal

color 

White to Gray to Brown

InChI

InChI=1S/C6H3BrF2O/c7-3-1-2-4(10)6(9)5(3)8/h1-2,10H

InChIKey

JZAVCMMYGSROJP-UHFFFAOYSA-N

SMILES

C1(O)=CC=C(Br)C(F)=C1F

CAS DataBase Reference

144292-32-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

25

Safety Statements 

45

RIDADR 

2811

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

HS Code 

2908190090

4-Bromo-2,3-difluorophenol Usage And Synthesis

Chemical Properties

white solid

Uses

4-Bromo-2,3-difluorophenol is used as medical intermediate.

Synthesis

The general procedure for the synthesis of 2,3-difluoro-4-bromophenol from 4-bromo-2,3-difluoroanisole was as follows: to a stirred solution of 1-bromo-2,3-difluoro-4-methoxybenzene (3 g, 13.45 mmol) in dichloromethane (DCM, 30 mL) was slowly added dropwise to a dichloromethane (DCM) solution of 1 M boron tribromide (BBr3) (26.9) at -20 °C. The dropwise addition time was controlled to 10 min. mL, 26.9 mmol), and the dropwise addition time was controlled over 10 min. The cooling bath was removed and the reaction mixture was continued to be stirred at room temperature for 12 hours. Subsequently, the reaction mixture was cooled to 10 °C and the reaction was quenched with saturated aqueous sodium bicarbonate solution (100 mL). The mixture was diluted with dichloromethane (DCM, 150 mL) and the organic layer was separated, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the target product 4-bromo-2,3-difluorophenol (2 g, 9.47 mmol, 70% yield) in the form of a dark red oil. NMR hydrogen spectrum (400MHz, chloroform-d): δ 7.15-7.21 (m, 1H), 6.69-6.76 (m, 1H), 5.30-5.31 (m, 1H) ppm.

References

[1] Patent: WO2017/59085, 2017, A1. Location in patent: Page/Page column 453

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