Hydrochloric Acid → 4-(2-(4-Bromophenoxy)ethyl)morpholine

Participants

Reaction Steps

To a solution of 4-bromophenol (3.30 g, 20.0 mmol), triphenylphoshine (5.25 g, 20.0 mmol) and N-(2-hydroxyethyl)morpholine (2.51 g, 19.1 mmol) in THF (30 mL) was added diisopropyl azodicarboxylate (3.94 mL, 20.0 mmol) over 10 min. The reaction mixture was stirred at room temperature for 2 h, and then hydrochloric acid (50 mL, 1N) was added. The mixture was extracted with diethyl ether (2×50 mL), and then the pH was adjusted to 10 with 2N aq. NaOH. The mixture was then extracted with ethyl acetate (2×50 mL) and the combined organic layers were dried over MgSO4 and concentrated under reduced pressure to afford N-(4-bromophenoxyethyl)morpholine (4.54 g, 15.9 mmol) as a white solid.

Provenance & Evidence