2-Bromoethanol → 1-[3-Chloro-5-[3-(4-fluoro-phenyl)-butoxy]-6-(2-hydroxy-ethoxy)-4-methoxy-2-methyl-phenyl]-ethanone

Participants

Reaction Steps

Example 7c (93 mg, 0.24 mmol) was reacted with 2-bromoethanol (1.5 eq.) as described under General Procedure F and the crude mixture was purified by flash chromatography (silica gel, Et2O/hexane 70:30) to afford the title compound (68 mg, 67%) as a pale yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.19-7.15 (m, 2H), 7.01-6.95 (m, 2H), 4.13-4.11 (m, 2H), 3.95 (d, J=6.8 Hz, 2H), 3.84 (s, 3H), 3.76-3.70 (m, 2H), 3.00 (m, 1H), 2.80 (t, J=6.5 Hz, 1H), 2.50 (s, 3H), 2.20 (s, 3H), 2.06-1.98 (m, 2H), 1.29 (d, J=6.9 Hz, 3H). MS (ES+) m/z 425.2 (M+H+).

Provenance & Evidence