反应详情

温度

0 °C

2-{[4-Chloro-3-(methyloxy)phenyl]methyl}-1H-isoindole-1,3(2H)-dione (7.0 g, 23 mmol) was dissolved in CH2Cl2 (25 mL) and cooled to 0° C. Boron tribromide (1.0 M sol., 46 mL) was added slowly then the solution was warmed to RT and stirred for 4 h. The reaction was cooled to 0° C. and ice water (100 mL) and EtOAc (200 mL) were added. The aqueous layer was separated and extracted with EtOAc (2×200 mL). The organic extracts were combined, dried over Na2SO4, filtered and evaporated. The solid was dissolved in EtOAc and washed with 1N NaOH. The aqueous layers were combined, acidified with 10% citric acid and extracted with EtOAc. The organic extracts were combined, dried over Na2SO4, filtered and evaporated to afford the title compound (3.0 g, 42%) as a tan solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 12.87 (br. s., 1H), 10.06 (s, 1H), 8.82 (t, 1H), 7.74 (d, 1H), 7.56 (dd, 1H), 7.47-7.54 (m, 1H), 7.45 (d, 1H), 7.23 (d, 1H), 6.94 (d, 1H), 6.80 (dd, 1H), 4.30 (d, 2H). MS: m/z 306.2 (M+1).

1. temperaturethe solution was warmed to RT
2. temperatureThe reaction was cooled to 0° C.
3. customThe aqueous layer was separated
4. extractionextracted with EtOAc (2×200 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. customevaporated
8. dissolutionThe solid was dissolved in EtOAc
9. washwashed with 1N NaOH
10. extractionextracted with EtOAc
11. dry with materialdried over Na2SO4
12. filtrationfiltered
13. customevaporated