反应详情

To 75 mmol of methylmagnesium bromide in 25 mL of ether stirring at 6° C. is added, dropwise over 10 min, a solution of methyl-3-bromobenzoate (4.3 g, 20 mmol) in 25 mL of dry THF. The mixture is then allowed to warm to ambient temperature and stirred for 3.5 h, then cooled to 0° C. and quenched by dropwise addition of aqueous 10% HCl. The acidified mixture is extracted twice with ethyl acetate, and the combined organic phases are washed with 1 N NaHCO3 and with brine. The solution is dried over Na2SO4, concentrated, and chromatographed over silica gel, eluting with 15% ethyl acetate in heptane, to afford 4.00 g (18.6 mmol, 93%) of 2-(3-bromophenyl)-2-propanol 27 as a pale yellow oil: 1H NMR (CDCl3) δ 7.65 (t, J=2 Hz, 1H), 7.39 (m, 2H), 7.20 (t, J=8 Hz, 1H), 1.78 (br s, 1H), 1.57 (s, 6H).

1. temperaturecooled to 0° C.
2. customquenched by dropwise addition of aqueous 10% HCl
3. extractionThe acidified mixture is extracted twice with ethyl acetate
4. washthe combined organic phases are washed with 1 N NaHCO3 and with brine
5. dry with materialThe solution is dried over Na2SO4
6. concentrationconcentrated
7. customchromatographed over silica gel
8. washeluting with 15% ethyl acetate in heptane