Yield:148583-65-7 98%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in ethanol;water; for 1 h;Sealed tube;Inert atmosphere;

Steps:

29 Preparation of 4-fluoro-2-iso ro ox benzenamine

A round-bottom flask was charged with 4-fluoro-2-isopropoxy-l -nitrobenzene (49.3 g, 248 mmol), EtOH (600 mL), and 10 % Pd/C (50 % in water, Degussa type E101; 10 g, 20wt% by weight of the starting nitro compound). The flask was sealed with a rubber septum, degassed, and back-filled with H₂ (x3) from a balloon filled with H₂. The reaction was stirred for 4 d using a H₂ filled balloon. The reaction mixture was filtered through a pad of celite, and the pad of celite was rinsed with MeOH. The filtrate was evaporated to dryness to provide 4-fluoro-2-isopropoxybenzenamine (41.0 g, 98%) as a brown liquid that was used without further purification. 1H NMR (300 MHz; ₆-DMSO) δ 6.67-6.72 (dd, 1H, J = 2.7Hz, 11Hz), 6.55-6.60 (dd, 1H, J = 6.0Hz, 8.7Hz), 6.43-6.49 (td, 1H, J = 2.7Hz, 8.4Hz), 4.47-4.55 (m, 3H), 1.23-1.25 (d, 6H, J = 6.0Hz); ¹⁹F NMR (282 MHz; ₆-DMSO) δ - 127.4 (sextet); m/z = 170 (M+H)⁺.

References:

WO2013/152198,2013,A1 Location in patent:Paragraph 00588