2-Amino-5-bromobenzaldehyde

90 g of compound III (0.39 mmol) was added to a 1 L round bottom flask, To the system was added 300 ml of absolute ethanol, 32 g of reduced iron powder (0.58 mol) was added under stirring, To the system was added 200 ml of 0.1 M HCl, Oil bath was heated to 80 , The reaction was carried out for 4 hours, The substrate reaction was complete, A portion of the ethanol was removed by rotary evaporation, Solid precipitation, Filtration, The solid was slurried with methylene chloride to obtain 71 g of a pale yellow powder of Compound III, Yield 92percent.HPLC analysis showed a purity of 97percent No further purification was required for the next reaction.1L round bottom flask was charged with 1B (9.7 g, 48.0 mmol), manganese dioxide (29 g, 336 mmol), dichloromethane(400 mL), stirred at room temperature for 3 h and the reaction was complete by TLC. Suction filtered, washed with dichloromethane, the combined filtrate, the solvent was evaporated under reduced pressure, 1C was obtained as a beige solid (7.3 g, 76.0percent yield).REFERENCE EXAMPLE 286 Step 2: Synthesis of 2-amino-5-bromobenzaldehyde A mixture of (2-amino-5-bromophenyl)methanol (10 g, 49.5 mmol) and Mn02 (25.8 g, 296.6 mmol) in CH2C12 (400 mL) was stuffed at RT overnight. LCMS showed the reaction was completed. The solid was filtered off, and the filtrate was concentrated to give the titlecompound as a light yellow solid (8 g, 8 1percent), which was directly used in next step without further purification. MS (ES+) C7H6BrNO requires: 199, found: 200, 202 [M + H].A mixture of (2-amino-5-bromophenyl)methanol (10 g, 49.5 mmol) and MnOA mixture of (2-amino-5-bromophenyl)methanol (10 g, 49.5 mmol) and MnO