反应详情

A mixture of 4-mercaptophenylboronic acid (1.0 g, 90%, 5.84 mmol), 1-bromo-3-methoxypropane (1.83 g, 11.7 mmol), K2CO3 (2.45 g, 17.5 mmol) and catalytic amount of Nal in CH3CN (20 mL) was stirred at ambient temperature overnight. After CH3CN was removed, water was added to the residue, and the mixture was extracted with CH2Cl2. The combined organic extract was washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give a milky oil. Water was added to this oily residue, and the aqueous layer was acidified to pH about 2 with concentrated HCl. The mixture was let stand at ambient temperature overnight, and the off-white solid was collected via filtration and washed with water and hexane to give 1.07 g (81%) of (4-{[3-(methoxy)propyl]thio}phenyl)boronic acid as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.98 (s, 2H), 7.68 (d, 2H, J=8.0 Hz), 7.22 (d, 2H, J=8.1 Hz), 3.38 (t, 2H, J=6.1 Hz), 3.19 (s, 3H), 2.98 (t, 2H, J=7.2 Hz), 1.85-1.70 (m, 2H); LRMS (ESI), m/z 225 (M−H).

1. customAfter CH3CN was removed
2. additionwater was added to the residue
3. extractionthe mixture was extracted with CH2Cl2
4. extractionThe combined organic extract
5. washwas washed with brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationthe filtrate was concentrated
9. customto give a milky oil
10. customat ambient temperature
11. customovernight
12. filtrationthe off-white solid was collected via filtration
13. washwashed with water and hexane