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ChemicalBook CAS DataBase List METHYL 2,4-DIFLUOROBENZOATE
106614-28-2

METHYL 2,4-DIFLUOROBENZOATE synthesis

6synthesis methods
2,4-Difluorobenzoic acid

1583-58-0

METHYL 2,4-DIFLUOROBENZOATE

106614-28-2

General procedure for the synthesis of methyl 2,4-difluorobenzoate from 2,4-difluorobenzoic acid: 1. 2,4-difluorobenzoic acid (1.5808 g, 10.00 mmol) was dissolved in methanol (15 mL) and cooled to 0 °C in an ice-water bath. 2. a methanol (10 mL) solution of thionyl chloride (1.46 mL, 20.02 mmol) was added slowly and dropwise to the above cooled mixture. 3. Gradually warm the reaction mixture to room temperature with continuous stirring for 24 hours. 4. Upon completion of the reaction, the mixture was poured into saturated aqueous NaHCO3 solution and extracted three times with ether. 5. The organic phases were combined and dried over anhydrous MgSO4. 6. The organic phase was concentrated under pressure and purified by silica gel column chromatography (eluent: hexane/ether=5/1) to give methyl 2,4-difluorobenzoate (1.6743 g, 97% yield). 7. The product was characterized by 1H-NMR (CDCl3): δ 7.99 (td, 1H, J=8.2,6.6 Hz), 6.98-6.84 (m, 2H), 3.93 (s, 3H).

-

Yield:106614-28-2 100%

Reaction Conditions:

at 20; for 2 h;

Steps:

6.1

To 100 mL of MeOH, 2,4-difluorobenzoyl chloride (10 mL, 79.3 mmol) was added and the mixture stirred at room temperature for 2 hours. The solvent was then evaporated affording the tilte compound as pale yellow oil (quantitative).IH-NMR (400 MHz), δ (ppm, DMSOtZ6): 8.0 (m, IH), 7.44 (m, IH), 7.25 (m, IH),3.87 (s, 3H).

References:

WO2007/68619,2007,A1 Location in patent:Page/Page column 97

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