5-Bromo-1-indanone → 5-bromo-2,3-dihydro-1H-inden-1-ol

To a solution of 5-bromo-2,3-dihydroinden-1-one (1.1 g, 5.2 mmol) in ethanol (100 mL) was added sodium borohydride (218 mg, 5.7 mmol). The mixture was stirred at room temperature for 24 hours. Then the resultant mixture was filtered. The filtrate was acidified with hydrochloric acid aqueous solution (1N) and the solvent was removed in vacuo. The residue was taken up with water (50 mL) and extracted with dichloromethane (50 mL). The combined organic phase was dried over sodium sulfate, filtered and concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=4:1) to give 5-bromo-2,3-dihydro-1H-inden-1-ol (1 g, 90%) as a yellow oil. LRMS (M+H+) m/z: calcd 211.98. found 211. 1H NMR (300 MHz, CDCl3): δ 7.40 (s, 1H), 7.37 (d, J=7.8 Hz, 1H), 7.27 (d, J=7.8 Hz, 1H), 5.22-5.18 (m, 1H), 3.09-2.99 (m, 1H), 2.86-2.76 (m, 1H), 2.55-2.46 (m, 1H), 2.01-1.76 (m, 1H), 1.75 (s, 1H).

1. filtrationThen the resultant mixture was filtered
2. customthe solvent was removed in vacuo
3. extractionextracted with dichloromethane (50 mL)
4. dry with materialThe combined organic phase was dried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customto give a residue
8. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=4:1)

ORD record

ord-10bd61543ab64eebbade8083f4ad1fb0

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206128B2