5-Fluoro-2-nitrotoluene

Chemical Properties

Industrial uses

Synthesis

352-70-5

446-33-3

The general procedure for the synthesis of 5-fluoro-2-nitrotoluene from 3-fluorotoluene is as follows: 1-fluoro-3-methylbenzene (9) (30 g, 273 mmol) was added slowly and dropwise to a stirred 90% aqueous nitric acid solution (100 mL) at 0-5 °C. The reaction mixture was stirred for 0.5 min and poured into ice water. The aqueous phase was extracted with dichloromethane (3 x 50 mL), the organic phases were combined and washed with saturated aqueous sodium bicarbonate (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution gradient: 0.5% to 3.3% ethyl acetate in petroleum ether) to afford the target product 5-fluoro-2-nitrotoluene as a yellow oil (16 g, 38% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 2.64 (s, 3H), 7.01-7.06 (m, 2H), 8.07 (m, 1H).

References