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2,5-Difluorophenylene-1,4-diamine, 1,4-Diamino-2,5-difluorobenzene synthesis

7synthesis methods
-

Yield: 88%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in methanol at 20; for 5 h;Inert atmosphere;

Steps:

3
To a solution of compound 3.4 (2.50 g, 14.36 mmol, 1 equiv) in MeOH (30 mL) was added Pd/C (600 mg, 10% purity) under N2. The suspension was degassed under vacuum and purged with H2 several times. The mixture was stirred under H2 (15 psi) at 20 °C for 5 hr. LC- MS showed compound 3.4 was consumed, and the main product was compound 3.5 (r.t. = 0.114 min, [M+H]+ = 144.7). The reaction mixture was filtered through a celite pad, and the filtrate was concentrated under reduced pressure to give compound 3.5 (1.82 g, 12.63 mmol. 88.0% yield) as a black-brown solid. NMR (400 MHz, DMSO-de): d 6.48 (t, J = 10.4 Hz, 2H), 4.45 (br s, 4H).

References:

FOG PHARMACEUTICALS, INC.;MCGEE, John, Hanney;THOMSON, Ty, Matthew;WAHL, Sebastian, Christof, Theodor;VERDINE, Gregory, L.;REZAEI ARAGHI, Raheleh;ZHANG, Yue-Mei;MULVIHILL, Mark Joseph WO2020/41270, 2020, A1 Location in patent:Paragraph 0352; 0356