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ChemicalBook CAS DataBase List 3-Amino-4-fluorophenol
62257-16-3

3-Amino-4-fluorophenol synthesis

13synthesis methods
Add 450ml water in the 5L reaction flask, 708.5g (10.9mol) zinc powder, 303g (1.09mol) 2-bromo-4-fluoro-5-amino-benzene oxygen ethyl formate, mix, 45 ℃ drip the solution that 218g (5.45mol) sodium hydroxide and 1500ml water are made into down, insulated and stirred is warming up to 60 ℃ after 1 hour to be incubated 4 hours after reactions more complete, the cooling suction filtration, getting filtrate dropping 406g (3.33mol) 30% hydrochloric acid separates product, filtration obtains brown solid, use ethyl alcohol recrystallization, get yellow solid 118.5g (0.93mol) 3-amino-4-fluorophenol after the drying. A molar yield of 85% is 99.5% through gas chromatography determination purity.136 ℃/20mmHg of boiling point.
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Yield: 90%

Reaction Conditions:

with palladium on activated charcoal;hydrogen in ethanol at 20; under 760.051 Torr; for 18 h;

Steps:

Step 1 . Synthesis of compound (233)
Palladium on activated charcoal (around 300mg) was added to a solution of 4-fluoro-3-nitro-phenol 232 (3.0g, 19.0mmol, 1 .Oeq) in ethanol (1 OOmL). The reaction mixture was hydrogenated at room temperature over 1 atmosphere of hydrogen for 18h. The reaction mixture was filtrated through a short pad of celite and rinsed with ethanol. The filtrate was evaporated to dryness to afford the expected compound 233 as brown sticky solid (Yield: 90%, 2.18g). The compound was used directly in the next step without further purification.

References:

ANAGENESIS BIOTECHNOLOGIES S.A.S. WO2021/13712, 2021, A1 Location in patent:Page/Page column 152

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