4-aMino-2-fluorobenzaldehyde synthesis

Yield:777089-27-7 85%

Reaction Conditions:

with iron;ammonium chloride in ethanol;water at 60; for 1 h;Inert atmosphere;

Steps:

45.1 Step 1. 4-amino-2-fluorobenzaldehyde

To a solution of 2-fluoro-4-nitrobenzaldehyde (CAS registry number 157701-72-9)(50 mg, 0.3 mmol) in EtOH (3 mL) and H20 (3 mL) were added Fe power (101 mg, 1.8mmol) and NH4C1 (95 mg, 1.8 mmol). Then the reaction was heated at 60 °C for 1 h under N2. TLC confirmed that starting material was consumed and a new product was formed. The mixture was diluted with H20 (30 mL) and extracted with EtOAc (30 mL x 2). The combined organic layer was dried over Na2SO4, filtered and concentrated to give 4-amino-2-fluorobenzaldehyde as a yellow solid (35 mg, 85%), which was used for the next step without purification. ‘H NIVIR (CDC13 400MHz): 5 10.08 (s, 1 H), 7.68 (t, J= 8.0 Hz, 1 H), 6.45 (dd, J= 8.4, 2.0 Hz, 1 H), 6.31 (dd, J= 12.4, 2.4 Hz, 1 H), 4.73 (s, 1 H), 4.40 (s, 1 H).

References:

WO2017/112768,2017,A1 Location in patent:Page/Page column 84