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).
