4-Amino-2,6-difluorophenol synthesis
- Product Name:4-Amino-2,6-difluorophenol
- CAS Number:126058-97-7
- Molecular formula:C6H5F2NO
- Molecular Weight:145.11
847861-84-1
126058-97-7
General procedure for the synthesis of 4-amino-2,6-difluorophenol from 2-(benzyloxy)-1,3-difluoro-5-nitrobenzene: To a solution of 2-(benzyloxy)-1,3-difluoro-5-nitrobenzene (5.3 g, 20 mmol) in ethanol (100 mL) was added 10% palladium/activated carbon (1.5 g). The reaction mixture was stirred overnight at room temperature and 1 atmosphere of hydrogen at 1 atm. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to afford 4-amino-2,6-difluorophenol (2.9 g, 95% yield). The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ 8.68 (br s, 1H), 6.19 (d, J = 10.8 Hz, 2H), 5.01 (s, 2H).
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Yield: 90.1%
Reaction Conditions:
with palladium 10% on activated carbon;hydrogen in methanol;water at 60 - 70; under 2250.23 - 3000.3 Torr;Sealed tube;Reagent/catalyst;
Steps:
1.4; 2.4 (4) Preparation of 4-amino-2,6-difluorophenol
General procedure: 350 g of 4-nitro-2,6-difluorophenol (2 mol), 2 L of methanol and 19 g of 5% palladium carbon (water content 54.13%) were successively added to the reaction vessel, sealed the kettle, air was exchanged in a high-purity hydrogen gas exchange tank, pressure 0.3-0.4 MPa, Heated and stirred, the temperature was controlled at 60-70 ° C, and the reaction was carried out for 3-5 h. Hydrogen is required when the pressure is less than 0.15 MPa. After the reaction was completed, it was cooled to room temperature, kettle was opened, subjected to suction filtration and recovered palladium on carbon. The filtrate was subjected to exsolution under reduced pressure, and then distilled under reduced pressure to give 4-amino-2,6-difluorophenol. The purity was 95.3% and the yield was 89.7%.The facts of the embodiment 1 of the synthesis method and conditions, (1), (2), (3), (5), (6) step reaction does not change, only the (4) in the step 5% palladium-carbon catalyst for the exchange 10% palladium-carbon catalyst, to obtain 4 - amino - 2, 6 - difluoro phenol, purity 95.8%, yield 90.1%.
References:
Ludong University;Liu Gang;Wang Haojie;Wang Jinming;Ren Yujin;Zhang Yuchun;Mu Xianfeng;Han Qinglin;Xu Zhenhua;Xu Guanhua CN109456224, 2019, A Location in patent:Paragraph 0014; 0017; 0019
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