反应详情

温度

0 °C

Isopropylmagnesium chloride-lithium chloride complex (8.35 mL, 10.9 mmol) was added to a cooled solution of 1-bromo-4-iodobenzene (3.07 g, 10.9 mmol) in THF (8 mL) and the resultant solution was stirred for 1 hour at 0° C. Methyl trans-4-acetylcyclohexanecarboxylate (1.00 g, 5.43 mmol) in THF (2 mL) was added to the reaction mixture, stirred for 1 hour at 0° C. and saturated aqueous ammonium chloride was added. The reaction mixture was extracted with ethyl acetate (2×), and then the combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified via silica gel column chromatography (ethyl acetate/hexanes) gave methyl trans-4-[1-(4-bromophenyl)-1-hydroxyethyl]cyclohexanecarboxylate as a colorless oil. MS ESI calcd. for C16H22BrO3[M+H]+341 and 343. found 341 and 343. 1H NMR (500 MHz, CDCl3) δ 7.44 (d, J=8.5 Hz, 2H), 7.26 (d, J=8.4 Hz, 2H), 3.63 (s, 3H), 2.16 (tt, J=12.3 Hz, 3.6 Hz, 1H), 2.03-1.91 (m, 2H), 1.84 (m, 1H), 1.60-1.53 (m, 2H), 1.52 (s, 3H), 1.36 (m, 2H), 1.11-0.98 (m, 2H).

1. extractionThe reaction mixture was extracted with ethyl acetate (2×)
2. dry with materialthe combined organic layers were dried over Na2SO4
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customThe residue was purified via silica gel column chromatography (ethyl acetate/hexanes)