Bis(2-chloroethyl) ether → HCID 58382401, compound

Participants

Reaction Steps

A flask was charged with 4-iodo-2-methylaniline (2.0 g, 8.6 mmol), 2,2′-dichloroethyl ether (2.45 g, 17.2 mmol), NH4Br (8.28 g, 25 mmol), and an aqueous NaOH solution (42 wt %, 4.10 g, 42.9 mmol). The mixture was refluxed overnight. The reaction mixture was cooled to rt and diluted with EtOAc (20 mL). The organic layer was separated, and the aqueous layer extracted with EtOAc (20 mL). The combined organic layers were washed with water (20 mL), dried over MgSO4 and concentrated under reduced pressure. The material was purified on silica gel eluting with 10:1 hexane/EtOAc to give 4-(4-iodo-2-methylphenyl)morpholine (1.3 g, 50%): 1H NMR (CDCl3, 400 MHz): 7.48 (d, J=8.4 Hz, 2H), 6.76 (s, 2H), 3.84-3.82 (m, 4H), 2.88-2.85 (m, 4H), 2.26 (s, 3H).

Provenance & Evidence