3-BROMO-4-FLUORO-BENZOIC ACID METHYL ESTER Chemical Properties

Melting point:

26-28

Boiling point:

245.3±20.0 °C(Predicted)

Density 

1.577±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to lump

color 

White to Orange to Green

InChI

InChI=1S/C8H6BrFO2/c1-12-8(11)5-2-3-7(10)6(9)4-5/h2-4H,1H3

InChIKey

JVORYGNKYAXATM-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

Hazard Note 

Irritant/Keep cold

HS Code 

2916310090

3-BROMO-4-FLUORO-BENZOIC ACID METHYL ESTER Usage And Synthesis

Chemical Properties

off-white powder

Synthesis

a) Synthesis of methyl 3-bromo-4-fluorobenzoate 3-Bromo-4-fluorobenzoic acid (3.33 g, 15.2 mmol) was dissolved in methanol (30 mL) and acetyl chloride (4.3 mL, 60.8 mmol) was added slowly and dropwise under cooling in an ice bath. The reaction mixture was stirred at room temperature for 20 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to afford methyl 3-bromo-4-fluorobenzoate (3.2 g, 90% yield) as a colorless oil.1H-NMR (CDCl3) δ: 3.92 (3H, s), 7.18 (1H, dd, J = 8.0, 8.2 Hz), 7.99 (1H, ddd, J = 1.9, 4.9, 8.0 Hz), 7.99 (1H, ddd, J = 1.9, 4.9, 8.0 Hz). 4.9, 8.0 Hz), 8.27 (1H, dd, J = 1.9, 6.5 Hz).

References

[1] European Journal of Medicinal Chemistry, 2007, vol. 42, # 11-12, p. 1334 - 1357
[2] Patent: US2010/280013, 2010, A1. Location in patent: Page/Page column 16
[3] Journal of Enzyme Inhibition and Medicinal Chemistry, 2012, vol. 27, # 5, p. 658 - 665,8
[4] Patent: WO2007/99171, 2007, A2. Location in patent: Page/Page column 55
[5] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 3, p. 358 - 362

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