2-Fluoro-6-nitrobenzoic acid methyl ester synthesis
- Product Name:2-Fluoro-6-nitrobenzoic acid methyl ester
- CAS Number:212189-78-1
- Molecular formula:C8H6FNO4
- Molecular Weight:199.14
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Yield:212189-78-1 94%
Reaction Conditions:
in methanol;dichloromethane at 0; for 0.5 h;
Steps:
Methyl 2-fluoro-6-nitrobenzoate. To 2-fluoro-6-nitrobenzoic acid (712 mg, 3.85 mmol) in methanol/acetonitrile (10 mL/10 mL) was dropwise added TMSCHN2 at 0° C. under N2 until yellow color persistent, and stirred additional 30 min. Then the reaction was quenched with HOAcat 0° C. until the yellow color disappears. Partial of the solvent was removed o rotary vacuum, the residue was dissolved in small amount of EtOAc, purified on flash chromatography eluting with 3050% EtOAc/hexanes (600 mL) to afford the expected product, methyl 2-fluoro-6-nitrobenzoate, (716 mg, 94% yield) which was used in step-2; 1H NMR (400 MHz, CDCl3) δ ppm 3.96 (s, 3H), 7.40-7.48 (m, 1H), 7.58 (td, J=8.31, 5.54 Hz, 1H), 7.94 (d, J=8.31 Hz, 1H); Mass spec. 200.05 (MH+), Calc. for C8H6FNO4 199.03.
References:
US2006/94707,2006,A1 Location in patent:Page/Page column 66
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