1-{2-[4-(6-Methoxy-3,4-dihydronaphthalen-1-yl)phenoxy]ethyl}pyrrolidine → 1-{2-[4-(2-Bromo-6-methoxy-3,4-dihydronaphthalen-1-yl)phenoxy]ethyl}pyrrolidine

Participants

Reaction Steps

Pyridinium bromide perbromide (21.22 g, 60.55 mmol) was added portionwise to a solution of 1-{2-[4(6-methoxy-3,4-dihydronaphthalen-1-yl)phenoxy]ethyl}pyrrolidine (23 g, 72 mmol) in THF (700 mL). The reaction was stirred for 60 h. The precipitate was filtered through a Celite pad with the aid of THF. The off-white solid was dissolved in CH2Cl2 and MeOH and was filtered away from the Celite. The organic solution was washed with 0.5 N aq HCl followed by satd NaHCO3 (aq). The organic solution was dried (MgSO4), filtered, and concentrated to provide a brown solid (21.5 g, 83%). 1H NMR (250 MHz, CDCl3): δ7.14 (d, J=8.7 Hz, 2 H), 6.97 (d, J=8.8 Hz, 2 H), 6.71 (d, J=2.2 Hz, 1 H), 6.55 (m, 2 H), 4.17 (t, J=6.0 Hz, 2 H), 3.77 (s, 3 H), 2.96 (m, 4 H), 2.66 (m, 4 H), 1.85 (m, 4 H).

Provenance & Evidence