Water → 1-(2-Azidoethoxy)-4-bromo-2-(trifluoromethyl)benzene

Participants

Reaction Steps

2-(4-Bromo-2-(trifluoromethyl)phenoxy)ethyl methanesulfonate (15.54 mmol, 5.643 g) and potassium carbonate (46.6 mmol, 6.44 g) were combined and stirred in DMF (50 ml). Sodium azide (46.6 mmol, 3.03 g) was added and the reaction stirred at room temperature overnight. Starting material remained. Reaction was heated to 60° C. for 5 hours. The reaction mixture was poured into water and diluted with EtOAc. The layers were separated and the organic dried over sodium sulfate and concentrated in vacuo. The resulting residue was purified by silica chromatography, eluting with a gradient of heptane—50/50 heptane/EtOAc to afford 1-(2-azidoethoxy)-4-bromo-2-(trifluoromethyl)benzene. (2.27 g)

Provenance & Evidence