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ChemicalBook CAS DataBase List 4-Amino-3-fluorophenol

4-Amino-3-fluorophenol synthesis

11synthesis methods
Using p-nitrophenol as raw material, after catalytic hydrogenation, a sulfonation reaction is performed first, and then a fluorine substitution reaction is performed to substitute the fluorine at the 3-position. Afterwards, a desulfonation reaction was carried out, and the target product 4-Amino-3-fluorophenol was obtained through extraction.
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Yield:399-95-1 100%

Reaction Conditions:

with hydrogen;palladium 10% on activated carbon in tetrahydrofuran;ethanol at 20; for 4.5 h;

Steps:

107

To a solution of 3-fluoro-4-nitrophenol (20 g) in ethanol (200 ml)-tetrahydrofuran (125 ml) was added 10% palladium carbon (6.0 g), followed by stirring under a hydrogen atmosphere at room temperature for 4.5 hrs. The mixture was filtered to remove the catalyst, which was washed with ethanol. The filtrate was concentrated under a reduced pressure to provide the titled compound (16.1 g, 100%) as a pale yellow solid. 1H-NMR Spectrum (DMSO-d6) δ (ppm): 4.38 (2H, m), 6.34 (1H, m), 6.43 (1H, m), 6.59 (1H, dd, J=8.4, 10.4 Hz), 8.78 (1H, s).

References:

US2005/277652,2005,A1 Location in patent:Page/Page column 72-73

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