3-bromo-4-propan-2-yloxyaniline

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Bromo-4-fluoronitrobenzene (1.0 eq) was added to a stirring solution of potassium carbonate (2.0 eq) in isopropanol. The solution was heated for 4 days at 80° C. The solution was cooled and filtered through Celite and the plug washed with EtOAc. The organic layer is then washed with brine and water, dried over MgSO4, filtered and concentrated to yield the desired product. Rt=8.72 min. The solution was cooled filtered through Celite the plug washed with EtOAc The organic layer is then washed with brine and water dried over MgSO4 filtered concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Platinum oxide (50 mg) was added to a solution of 2-isopropoxy-5-nitrobromobenzene (1.7 g, 6.5 mmol) in ethyl acetate (50 ml) and the mixture was stirred under hydrogen (50 psi) for 1 hour. The mixture was filtered, further platinum oxide (50 mg) was added and the mixture was stirred under hydrogen (50 psi) for 1 hour. The mixture was filtered and the solvent was evaporated under reduced pressure. The residue was purified by flash chromatography, eluting with hexane/EtOAc (80:20), to give the title compound (0.92 g, 62%); δH (360MHz, CDCl3) 1.32 (3H, d, J 5.6Hz, OCH(CH3)2), 4.33 (1H, m, OCH(CH3)2), 6.57 (1H, dd, J 8.7, 2.8Hz, 6-H), 6.78 (1H, d, J 8.7Hz, 5-H), 6.91 (1H, d, J 2.8 Hz, 2-H). The mixture was filtered further platinum oxide (50 mg) was added the mixture was stirred under hydrogen (50 psi) for 1 hour The mixture was filtered the solvent was evaporated under reduced pressure The residue was purified by flash chromatography eluting with hexane/EtOAc (80:20)