4-Nitrophenol → 1-Nitro-4-(2,2,2-trifluoroethoxy)benzene

Participants

Reaction Steps

To prewashed sodium hydride (0.61 g, 25.5 mmol) in 10 ml of hexamethylphosphorotriamide (HMPT) is added 4-nitrophenol (3.55 g, 25.5 mmol) in 10 ml of HMPT at 25°-30°. Five ml more of HMPT is added and the mixture is warmed gently to 45°-50° for 30 min. 2,2,2-Trifluoroethyl methansulfonate (5.0 g, 28.0 mmol) and HMPT (1 ml) are then added and the mixture is heated to 146°-151° for 20 hours. The reaction mixture is cooled to RT and is then poured into ice water and extracted with ether (3X). The combined ether layers are washed with water and brine, dried, filtered and rotoevaporated to give 4-(2,2,2-trifluoroethoxy)nitrobenzene.

Provenance & Evidence