1,3-Dibromopropane → HCID 67145241, compound

Participants

Reaction Steps

A mixture of 1-(4-hydroxyphenyl)propan-2-one (1 g, 6.67 mmol), 1,3-dibromopropane (0.74 mL, 7.3 mmol) and potassium carbonate (1.84 g, 13 3 mmol) in 2-butanone (30 mL) was heated to reflux for 16 hours. The reaction mixture was cooled to ambient temperature and partitioned between ethyl acetate and water. The organic phase was separated, and the aqueous phase was extracted with additional ethyl acetate. The organic extracts were combined, washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue obtained was chromatographed on silica gel eluting with 10% ethyl acetate/hexanes to provide the title compound: 1H NMR (300 MHz, CDCl3) δ ppm 2.14 (s, 3H), 2.36-2.27 (m, 2H), 3.60 (t, J=6.4 Hz, 2H), 3.63 (s, 2H), 4.09 (t, J=5.8 Hz, 2H), 6.87 (d, J=8.7 Hz, 2H), 7.11 (d, J=8.7 Hz, 2H); MS (DCI/NH3) m/z 288 (M+NH4)+.

Provenance & Evidence