2-Bromo-3-fluoro-6-nitrophenol

B. A solution of 2-bromo-1, 3-difluoro-4-nitrobenzene (10.5 g, 44.1 mmol) in DMSO (80 mL) was stirred at room temperature. To a mixture of B. 3-Bromo-4-fluoro-2-hydroxy-1-nitrobenzene A solution of 3-bromo-2, 4-difluoro-1-nitrobenzene (10.5 g, 44 mmol) in dimethyl sulfoxide (85 ml) was stirred at ambient temperature. A solution of potassium hydroxide (14.1 g, 251 mmol) in water (21 ml) was added dropwise over 15 minutes. The black reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was then poured onto water (200 ml) and three ether extractions (100 ml) were performed. The aqueous layer was acidified with concentrated hydrochloric acid and extracted three times with ether (100 ml). The combined organic layers were dried over magnesium sulfate and filtered. Solvent was removed in vacuo to give a yellow solid (9.7 g, 93percent yield). Recrystallization from isopropyl ether afforded an analytical sample: m.p. 65°-66° C. NMR (CDCl3, 60 MHz): 8.1 (dd, 1H, J=10, 5 Hz), 6.8 (dd, 1H, J=10, 8 Hz) Anal.: Calcd. for C6H3BrFNO3: C, 30.54, H, 1.30, N, 5.94, Br, 33.86, F, 8.05. Found: C, 30.52, H, 1.27, N, 5.70, Br, 33.56, F, 7.96.A solution of 2-bromo-1, 3-difluoro-4-nitrobenzene (10.5 g, 44.1 mmol) in DMSO (80 mL) was stirred at room temperature. Then, a solution of KOH (12.4 g, 221 mmol) in water (22 mL) was added dropwise over 15 minutes. After the addition, the mixture was stirred overnight at 30°C. Completion of the reaction was determined by TLC. The mixture was acidified with 2 N HCl to pH 4, and ethyl acetate (100 mL x 2) was added to the mixture for extraction of the desired compound. The combined organic layer was washed with water and brine, dried over Na2SO4, and concentrated to give C. 1-(2-Bromo-3-fluoro-6-nitrophenoxy)-propan-2-one Chloroacetone (3.8 g, 3.3 ml, 41 mmol) was added dropwise to a solution of