2-Fluoro-5-methyl-4-nitrophenol

Synthesis

Added 2-fluoro-5-methylphenol (0.200 g, 1.59 mmol) to a 5 mL flask followed by AcOH (0.40 mL) and H2SO4 (0.058 mL) at 0 ⁰C (ice-salt bath). Then sodium nitrite (0.29 mL of 5.5 M in water) was slowly added to the reaction to give a burnt orange color. The reaction was stirred for 30 min on the ice bath. Poured reaction over ice and then filtered off a light orange solid. Warmed 20% nitric Acid in water (5 mL) to 45 ⁰C then added the orange solid in portions while stirring. The reaction was stirred for twenty min then diluted with water and cooled. The light orange solid was filtered off to give 2-fluoro-5-methyl- 4-nitrophenol as a light orange solid (0.124g, 46% yield). 1H NMR (500 MHz, DMSO-d6) δ 13.86 (s, 1H), 7.42 (d, J = 11.6 Hz, 1H), 6.47 (dq, J = 8.2, 1.3 Hz, 1H), 2.23 (d, J = 1.3 Hz, 3H).