2-Carboxy-5-fluoro-4-nitrotoluene, 5-Carboxy-2-fluoro-4-methylnitrobenzene synthesis
- Product Name:2-Carboxy-5-fluoro-4-nitrotoluene, 5-Carboxy-2-fluoro-4-methylnitrobenzene
- CAS Number:64695-92-7
- Molecular formula:C8H6FNO4
- Molecular Weight:199.14
321-21-1
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Yield: 84%
Reaction Conditions:
with nitric acid;sulfuric acid at 0; for 0.75 h;
Steps:
62.1
Example 62.2-[2-(1 ,3-benzothiazol-5-yl)-1 H-imidazol-4-yl]-N,N,6-trimethyl-1-[2-(methyloxy)ethyl]-1 H- -5-carboxamideStep 1 . 4-fluoro-2-methyl-5-nitrobenzoic acid: nitric acid (0.4 ml, 8.06 mmol) was added to a stirred solution of 4-fluoro-2-methylbenzoic acid (1 g, 6.49 mmol) in sulfuric acid (4.7 ml, 88 mmol) at 0°C. Stirred for 45 mins, diluted with ethyl acetate and poured into ice water. The aqueous phase was extracted with EtOAc twice, the combined EtOAc layers were washed with brine, dried over sodium sulfate. The EtOAc layer was concentrated, and purified via Biotage (SNAP Cartridge KP Sil 25 g, 0-5% Methanol/Dichloromethane, 1 % Acetic acid) to yield 4-fluoro-2-methyl-5-nitrobenzoic acid (1 .08 g, 5.42 mmol, 84 % yield). 1H NMR (600 MHz, CDCI3) δ 8.85 (d, J = 7.55 Hz, 1 H), 7.24 (d, J = 1 1.33 Hz, 1 H), 2.76 (s, 3 H); MS (m/z) 200.1 (M+H)+.
References:
GLAXO GROUP LIMITED;BODMER, Vera, Q.;CASILLAS, Linda, N.;DEMARTINO, Michael, P.;KING, Bryan, W.;LAKDAWALA SHAH, Ami;LEISTER, Lara, Kathryn;WANG, Gren, Z.;WISNOSKI, David, Duff;HARRIS, Philip, A.;RAMANJULU, Joshi, M.;ROMANO, Joseph, J.;WILSON, Matthew, A. WO2011/123609, 2011, A1 Location in patent:Page/Page column 67
321-21-1
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$6.00/1g
64695-92-7
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$45.00/100mg
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64695-92-7
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