反应详情

To a solution of 7-bromo-3,4-dihydro-2H-naphthalen-1-one (CAS#32281-97-3, 3.5 g, 0.015 mol) in methanol (7 mL) and dichloromethane (10 mL) at 0° C. is added sodium borohydride (1.47 g, 0.038 mol) in one portion. The cooling bath is removed and after 1.5 hours, the mixture is poured into water and the volatile organics are removed in vacuo. Extraction with dichloromethane, drying over sodium sulfate, filtering through a cotton plug and concentration in vacuo affords 7-bromo-1,2,3,4-tetrahydro-naphthalen-1-ol. 1H NMR (400 MHz, CDCl3) δ ppm 1.72 (d, J=6.3 Hz, 1 H), 1.74-1.90 (m, 2 H), 1.92-2.07 (m, 2 H), 2.62-2.71 (m, 1 H), 2.73-2.82 (m, 1 H), 4.73-4.77 (m, 1 H), 6.98 (d, J=8.2 Hz, 1 H), 7.31 (dd, J=8.2, 2.1 Hz, 1 H), 7.61 (d, J=2.1 Hz, 1 H).

1. customThe cooling bath is removed and after 1.5 hours
2. additionthe mixture is poured into water
3. customthe volatile organics are removed in vacuo
4. extractionExtraction with dichloromethane
5. dry with materialdrying over sodium sulfate
6. filtrationfiltering through a cotton plug and concentration in vacuo