| Identification | Back Directory | [Name]
METHYL 2-FLUORO-5-NITROBENZOATE | [CAS]
2965-22-2 | [Synonyms]
RARECHEM AL BF 0280
METHYL 2-FLUORO-5-NITROBENZOATE
Methyl2-fluoro-5-nitrobenzoate,98%
4-Fluoro-3-(Methoxycarbonyl)nitrobenzene
methyl 2-fluoro-5-nitrobenzenecarboxylate
5-nitro-2-fluorobenzoic acid methyl ester
Benzoic acid, 2-fluoro-5-nitro-, methyl ester | [Molecular Formula]
C8H6FNO4 | [MDL Number]
MFCD06203689 | [MOL File]
2965-22-2.mol | [Molecular Weight]
199.14 |
| Chemical Properties | Back Directory | [Melting point ]
49-51℃ | [Boiling point ]
303℃ | [density ]
1.388 | [Fp ]
137℃ | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
soluble in Methanol | [form ]
Solid | [color ]
White to Yellow to Green |
| Hazard Information | Back Directory | [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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