ChemicalBook CAS DataBase List 3-Fluoro-4-nitroaniline

3-Fluoro-4-nitroaniline synthesis

11synthesis methods

Product Name:3-Fluoro-4-nitroaniline
CAS Number:2369-13-3
Molecular formula:C6H5FN2O2
Molecular Weight:156.11

N-(3-fluoro-4-nitrophenyl)-2,2-dimethyl-

1152311-98-2
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2369-13-3
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Yield:2369-13-3 99%

Reaction Conditions:

Stage #1:N-(3-fluoro-4-nitro-phenyl)-2,2-dimethyl-propionamide with hydrogenchloride in dichloromethane;water for 2 h;Reflux;
Stage #2: with potassium carbonate in dichloromethane;water;ethyl acetate

Steps:

9.a
A mixture of N-(3-fluoro-4-nitro-phenyl)-2, 2-dimethyl-propionamide (87.0 g, 0.36 mol) in CH₂Cl₂ (400 mL) and 6N hydrochloric acid (800 mL) was heated to reflux for 2 hours. The reaction mixture was cooled to room temperature. The reaction mixture was diluted with 1000 mL of ethyl acetate and potassium carbonate (500.0 g) was added portion wise. The aqueous solution was separated and the organic layer was washed with brine and dried over anhydrous Na₂SO₄. The solvent was removed by evaporation under reduced pressure; the residue was purified by column chromatography on silica gel (petroleum ether / ethyl acetate 30: 1) to afford 3-fluoro-4-nitroaniline (56.0 g, 99 %). ¹H NMR (300 MHz, CDCl₃) δ 8.07 (t, J = 8.7 Hz, 1 H), 7.86 (dd, J= 2.1, 13.2 Hz 1 H), 7.59 (brs, 2 H), 7.22 (s, 1 H).

References:

VERTEX PHARMACEUTICALS INCORPORATED;RUAH, Sara, Hadida, S.;GROOTENHUIS, Peter, D., J.;VAN GOOR, Fredrick;MILLER, Mark, T.;MCCARTNEY, Jason;ZHOU, Jinglan;BEAR, Brian;NUMA, Mehdi, Michel, Djamel WO2010/53471, 2010, A1 Location in patent:Page/Page column 56

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