4-Bromo-2-ethoxy-1-nitrobenzene

General procedure: Preparation 100: 4-bromo-2-ethoxy-1 -nitrobenzene To a cooled (0°C) solution of EtOH (0.07 mL, 1 .193 mmol) in THF (5 mL) was added NaH (60percent suspension in mineral oil, 68 mg, 1 .705 mmol). The reaction mixture was stirred under nitrogen at 0 for 15 minutes. 2-fluoro-4-bromo-nitrobenzene (250 mg, 1 .136 mmol) was added and the reaction mixture stirred for a further 18 hours, whilst warming slowly to room temperature. The reaction mixture was concentrated in vacuo. Ether (20 mL) and HCI (0.5 M, 20 mL) were added. The aqueous layer was basified with aqueous saturated NaHC04-Bromo-2-fluoro-1-nitro-benzene (15.0 g, 68.2 mmol) was dissolved in ethanol (150 ml), and sodium ethoxide (14.0 g, 205 mmol) was added thereto, followed by stirring at room temperature for 2 hours. The reaction liquid was concentrated under reduced pressure, and then diluted with water. The precipitated solid was filtered and dried under reduced pressure to obtain the title compound (16.0 g, 95percent). [1293] 62A: 4-bromo-2-ethoxy-l-nitrobenzene; [00479] To a solution of 4-bromo-2-fluoro-l-nitrobenzene (3 g, 13.6 mmol) and EtOH (50 mL) was added NaOEt (21percent w/w, 50 mL). The mixture stirred for 2 h before concentrating in vacuo. The residue purified by flash chromatography (0- 100percent EtoAc/Hexane) to afford 62A (3 g, 90percent) as an oil.