Methyl iodide → 3-Fluoro-4-nitroanisole

Participants

Reaction Steps

28 g (0.2 mole) of 3-fluoro-4-nitrophenol was dissolved in 200 mL of acetone. 56 g (0.4 mole) of K2CO3 was added, and the contents heated to 40 C for 10 min. Contents were cooled to 0 C, 25 mL (0.4 mole) of methyl iodide added, and again heated to 40 C for 3 hrs. Reaction cooled to rt, roto-evaporated to approx. 100 mL, and 200 mL of methylene chloride was added. Contents were filtered, and the filtrant was rotary-evaporated to dryness. The crystalline solid was recrystallized from 4:1 EtOH/H2O to give 23.6 g (46%) of desired product. 1H NMR (CDCl3, 400 MHz) 8.12 (m, 1H), 6.78 (m, 2H), 3.93 (s, 3H); LCMS (M+H)+ 172 found.

Provenance & Evidence