Ethyl 4-fluoro-2-nitrophenylacetate synthesis
- Product Name:Ethyl 4-fluoro-2-nitrophenylacetate
- CAS Number:1209007-72-6
- Molecular formula:C10H10FNO4
- Molecular Weight:227.19
1209007-71-5
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1209007-72-6
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Yield:1209007-72-6 75%
Reaction Conditions:
with toluene-4-sulfonic acid in toluene; for 4 h;Reflux;
Steps:
Ethyl (4-fluoro-2-nitrophenyl)acetate (42).
To a solution of 41 (2.19 g, 6.69 mmol) in toluene (13.0 ml) was added p-toluenesulfonic acid mono hydrate (127 mg, 0.669 mmol) and the mixture was refluxed for 4 h. After the concentration in vacuo, the residue was added ethyl acetate. The organic layer was washed with sat. sodium bicarbonate aqueous solution and brine, then dried over anhydrous magnesium sulfate. The solvent was removed in vacuo, the residue was purified by NH silica gel column chromatography (20% ethyl acetate/n-Hexane) to afford 42 (1.14 g, 75%) as a yellow oil. 1H NMR (600MHz, CDCl3) δ 1.27 (3 H, t, J = 7.1 Hz), 4.00 (2H, s), 4.18 (2H, q, J = 7.3 Hz), 7.30-7.40 (2H, m), 7.86 (1H, dd, J = 8.5, 2.5 Hz); MS (ESI): m/z 226 [M-H]-.
References:
Chonan, Tomomichi;Wakasugi, Daisuke;Yamamoto, Daisuke;Yashiro, Miyoko;Oi, Takahiro;Tanaka, Hiroaki;Ohoka-Sugita, Ayumi;Io, Fusayo;Koretsune, Hiroko;Hiratate, Akira [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 5,p. 1580 - 1593] Location in patent:supporting information; experimental part
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