p-Fluoronitrobenzene → Pyridine, 4-(4-nitrophenoxy)-2-(trifluoromethyl)-

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-trifluoromethyl-pyridin-4-ol (0.675 g, 4.14 mmol), 1-fluoro-4-nitro-benzene (0.54 mL, 4.97 mmol, 1.2 equiv), and NaOH (0.203 g,4.97 mmol, 1.2 equiv) in DMF abs. is heated to 100° C. (oil bath temperature) for 21.5 h, under an argon atmosphere. The reaction mixture is allowed to cool to rt, filtered through a glass sintered funnel and concentrated in vacuo. The residual yellow solid is purified by silica gel (100 g) column chromatography (CH2Cl2/hexane, 70/30) to afford the title compound as a white solid: ES-MS: 285.0 [M+H]+; single peak at tR=8.71 min (System 2); Rf=0.25 (CH2Cl2/hexane, 70/30).

Provenance & Evidence