Hydrogen Bromide → (S)-3-ethylmorpholine hydrobromide

Participants

Reaction Steps

(S)-3-ethyl-4-tosylmorpholine (220 mg, 0.82 mmol) and phenol (150 mg, 1.6 mmol) were dissolved in 4.1 M of hydrogen bromide in acetic acid (2.4 mL) and the solution was stirred at room temperature overnight. The reaction was poured on ether and the solid was collected by filtration and washed with ether to give (S)-3-ethylmorpholine hydrobromide (j-1) as a white solid: 1H NMR (400 MHz, CDCl3) δ 3.77-3.60 (m, 3H), 3.60-3.44 (m, 2H), 3.44-3.19 (m, 3H), 1.67 (dtd, J=28.6, 14.0, 7.4 Hz, 2H), 1.31-1.12 (m, 2H), 0.97-0.84 (m, 3H).

Provenance & Evidence