4-FLUORO-2-METHOXYBENZOIC ACID METHYL ESTER Chemical Properties

Melting point:

134-136°C

Boiling point:

232℃

Density 

1.184

Flash point:

91℃

storage temp. 

Sealed in dry,Room Temperature

form 

solid

Appearance

Off-white to yellow Solid-Liquid Mixture

InChI

InChI=1S/C9H9FO3/c1-12-8-5-6(10)3-4-7(8)9(11)13-2/h3-5H,1-2H3

InChIKey

LJUAEPNTXDJBRX-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC=C(F)C=C1OC

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2916310090

4-FLUORO-2-METHOXYBENZOIC ACID METHYL ESTER Usage And Synthesis

Uses

Methyl 4-fluoro-2-methoxybenzoate ?is used as a catalyst, kinase inhibitors and pharmaceutical intermediates.

Synthesis

General procedure for the synthesis of methyl 4-fluoro-2-methoxybenzoate from methanol and 4-fluoro-2-methoxybenzoic acid: 4-fluoro-2-methoxybenzoic acid (1.7 g, 10 mmol) was dissolved in methanol (100 mL) at 0 °C and thionyl chloride (5.73 g, 48 mmol) was added slowly. The reaction mixture was stirred at room temperature for 12 hours. Upon completion of the reaction, the solvent was removed by rotary evaporator under vacuum. Saturated aqueous sodium bicarbonate (50 mL) was added to the residue to neutralize the unreacted thionyl chloride, followed by extraction with ethyl acetate (100 mL x 3). The organic phases were combined and dried over anhydrous sodium sulfate. The desiccant was removed by filtration and the filtrate was concentrated under vacuum to afford the target product methyl 4-fluoro-2-methoxybenzoate (1.3 g, 70% yield).

References

[1] Patent: CN106146493, 2016, A. Location in patent: Paragraph 0534; 0535; 0536; 0537
[2] Patent: WO2013/75083, 2013, A1. Location in patent: Paragraph 00254; 00255
[3] Patent: US9206128, 2015, B2. Location in patent: Page/Page column 135; 136

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