反应详情

温度

0 °C

280 ml of 1M Borane-THF complex was added dropwise to a stirred solution of 4-bromophthalimide (20.85 g; 92.2 mmol) in anhydrous THF (200 ml) at 0° C. then heated at reflux overnight. The reaction was cooled to 0° C. then treated cautiously with methanol (100 ml) followed by 2M HCl (100 ml) then heated at reflux for 3 hours. The reaction mixture was cooled and the organics evaporated. The aqueous was diluted with water (100 ml) the extracted with DCM (×3). The aqueous was basified with 2M NaOH then extracted with DCM (×3). The combined DCM extracts were dried (MgSO4), filtered and evaporated to give 6.99 g of 5-bromo-2,3-dihydro-1H-isoindole as a dark brown gummy solid. 1H NMR (DMSO-d6) 7.45 (1H, s), 7.36 (1H, d), 7.20 (1H, d), 4.05 (4H, s).

1. temperaturethen heated
2. temperatureat reflux overnight
3. temperaturethen heated
4. temperatureat reflux for 3 hours
5. temperatureThe reaction mixture was cooled
6. extractionextracted with DCM (×3)
7. extractionthen extracted with DCM (×3)
8. dry with materialThe combined DCM extracts were dried (MgSO4)
9. filtrationfiltered
10. customevaporated