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ChemicalBook CAS DataBase List 4-Fluoroaniline
371-40-4

4-Fluoroaniline synthesis

11synthesis methods
The better process in the one-step process is the nitrobenzene method, which is obtained by deoxygenation, hydrogenation and fluorination. With PdCl2-V2O5 as the catalyst and carbon monoxide as the reducing agent, the reaction was carried out at 160°C for 3h, and the yield of 4-fluoroaniline could reach 90%, with another 10% of aniline as a by-product. With PtO2 as the catalyst, BF3-HF as the fluorinating agent and hydrogen as the reducing agent, the reaction was carried out at 42℃ for 12.5h, with 100% conversion and 95% yield.
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Yield:371-40-4 100%

Reaction Conditions:

with 10% Pd/C;hydrogen in methanol at 20; for 3 h;

Steps:

2 4.2.2. 4-Fluoroaniline (4a)

To a solution of 4-fluoro-1-nitrobenzene (3a, 212 mL, 2.00 mmol)in MeOH (10 mL) was added 10% Pd/C (21 mg, 0.020 mmol). Thereaction mixture was stirred and bubbled with H2 at room temperaturefor 3 h. The solids were filtered off and washed with DCM(25 mL). The filtrate and DCM washing were combined andconcentrated under reduced pressure to give 4a as a clear yellow oil(222 mg, 100%).

References:

Teo, Theodosia;Yang, Yuchao;Yu, Mingfeng;Basnet, Sunita K.C.;Gillam, Todd;Hou, Jinqiang;Schmid, Raffaella M.;Kumarasiri, Malika;Diab, Sarah;Albrecht, Hugo;Sykes, Matthew J.;Wang, Shudong [European Journal of Medicinal Chemistry,2015,vol. 103,p. 539 - 550]

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