反应详情

温度

-78 °C

To a −78° C. solution of 4-bromoanisole (0.45 mL, 3.6 mmol) in tetrahydrofuran (15 mL) was n-butyllithium (2.5 M in hexane, 1.3 mL, 3.3 mmol) added, after 0.5 h a solution of N-[(3-bromophenyl)(2-cyanophenyl)methylene]-2-methylpropane-2-sulfinamide (Scheme #5, N) (1.2 g, 3.0 mmol) in tetrahydrofuran (5 mL) was added. The reaction mixture was stirred at −78° C. for 3 h and then quenched by addition of water. Ethyl acetate was added and the mixture was washed with water and brine, dried over magnesium sulfate and concentrated. The residue was dissolved in methanol (25 mL) and treated with hydrochloric acid (2 M in diethyl ether, 3.0 mL, 6.0 mml) over night. The reaction mixture was concentrated and then partitioned between aqueous saturated sodium bicarbonate and chloroform, the organic phase was dried over magnesium sulfate and concentrated. Purification by column chromatography using a gradient of methanol in dichloromethane gave the title compound (0.70 g, 59%). 1H NMR (CDCl3) δ 7.57-7.48 (m, 3 H), 7.47-7.41 (m, 1 H), 7.39-7.32 (m, 2 H), 7.32-7.28 (m, 1 H), 7.26-7.20 (m, 2 H), 7.10 (t, J=7.83 Hz, 1 H), 6.83-6.77 (m, 2 H), 5.86 (br s, 2 H), 3.75 (s, 3 H); MS (AP) m/z 393, 395 [M+1]+.

1. customTo a −78° C.
2. additionwas added
3. customquenched by addition of water
4. additionEthyl acetate was added
5. washthe mixture was washed with water and brine
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated
8. dissolutionThe residue was dissolved in methanol (25 mL)
9. additiontreated with hydrochloric acid (2 M in diethyl ether, 3.0 mL, 6.0 mml) over night
10. concentrationThe reaction mixture was concentrated
11. custompartitioned between aqueous saturated sodium bicarbonate and chloroform
12. dry with materialthe organic phase was dried over magnesium sulfate
13. concentrationconcentrated
14. customPurification by column chromatography