METHYL 2-FLUORO-5-NITROBENZOATE Chemical Properties

Melting point:

49-51℃

Boiling point:

303℃

Density 

1.388

Flash point:

137℃

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

Solid

color 

White to Yellow to Green

Safety Information

HazardClass 

IRRITANT

HS Code 

2916399090

METHYL 2-FLUORO-5-NITROBENZOATE Usage And Synthesis

Synthesis

General procedure for the synthesis of methyl 2-fluoro-5-nitrobenzoate from methanol and 2-fluoro-5-nitrobenzoic acid: 1. dissolve 2-fluoro-5-nitrobenzoic acid (3.7 g, 20.0 mmol) in methanol (100 mL) at 0 °C. 2. Slowly add thionyl chloride (5.3 mL, 60.0 mmol) dropwise. 3. The reaction mixture was heated to reflux for 24 hours. 4. Upon completion of the reaction, the solvent was removed by vacuum concentration. 5. 5. The residue was dissolved in ethyl acetate and washed several times with 1.0 M NaOH solution. 6. The organic phase was dried with anhydrous sodium sulfate and the solvent was evaporated in vacuum to give the intermediate methyl 2-fluoro-5-nitrobenzoate (Intermediate 37) as a yellow oil, which crystallized into light yellow needle crystals after standing. Yield: 90%; Melting point: 47-49°C; 1H NMR (300MHz, CDCl3) δ= 4.01 (s, 3H, OCH3), 7.35 (t, 1H, H3,3JH3.H4 = 3JH3.F = 9.2Hz), 8.44 (dt, 1H, 3JH4-H3 = 9.2Hz, 4JH4.F = 4JH4-H6 = 3.5Hz), 8.87 (dd, 1H. 4JH6-F = 5.9 Hz, 4JH6-H4 = 2.7 Hz); 13C NMR (75 MHz, CDCl3): δ= 47.7 (OCH3), 113.2 (d, C3,2JC-F = 25.1 Hz), 114.5 (d, C1, 2JC-F = 12.0 Hz), 122.9 (d, C6,3JC-F = 3.3 Hz), 124.3 (d, C4,3JC-F = 10.9 Hz ), 138.6 (C5), 157.4 (d, COOCH3,3JC-F = 3.8 Hz), 159.8 (d, C2,1JC-F = 269.0 Hz).

References

[1] Patent: WO2012/85003, 2012, A1. Location in patent: Page/Page column 83-84
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 11, p. 4640 - 4660
[3] Patent: EP3192791, 2017, A1. Location in patent: Paragraph 0467
[4] Patent: WO2009/80836, 2009, A2. Location in patent: Page/Page column 70
[5] Patent: WO2004/92124, 2004, A2. Location in patent: Page 77

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