反应详情

To a solution of (4-isopropoxy-3-(trifluoromethyl)phenyl)methanol (181 g, 773 mmol) in toluene (1 L) was added SOCl2 (338 mL, 4637 mmol) (slight exotherm to 35° C. after addition of SOCl2) and was stirred overnight in a 2-L round bottomed flask. The reaction mixture was concentrated in vacuo and diluted with hexanes (1 L). The solution was washed with sat. NaHCO3 (2×750 mL), dried over MgSO4, and filtered. The solvents were removed under reduced pressure to give 4-(chloromethyl)-1-isopropoxy-2-(trifluoromethyl)benzene (194 g, 768 mmol, 99% yield) as an orange oil. Optionally the product can be further purified by distillation (bp=85° C. at 0.1 mTorr) to obtain a clear oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.37 (d, J=6.1 Hz, 6 H), 4.56 (s, 2H) 4.65 (sep, J=6.1 Hz, 1 H), 6.98 (d, J=8.6 Hz, 1 H), 7.48 (dd, J1=8.6, J2=2.3 Hz, 1 H), 7.57 (d, J=2.2 Hz, 1 H).

1. concentrationThe reaction mixture was concentrated in vacuo
2. additiondiluted with hexanes (1 L)
3. washThe solution was washed with sat. NaHCO3 (2×750 mL)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. customThe solvents were removed under reduced pressure