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

To a suspension of 40 g (184 mmol) of 5-bromo-1-indanone in 500 mL of methanol in a water bath was added 16.2 g of sodium borohydride portionwise, keeping the reaction temperature below 40° C. The water bath was removed and the reaction mixture stirred at ambient temperature for 2 h and then quenched by the addition of 100 mL of water. The methanol was removed in vacuo, and the residue partitioned between water and ethyl acetate. The aqueous phase was extracted with two portions of ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, and concentrated to give a yellow solid which was used without further purification. Mass spectrum (MS): m/z 195, 197 (M+1-H2O), 116 (M+1-H2O-HBr).

1. customthe reaction temperature below 40° C
2. customThe water bath was removed
3. customquenched by the addition of 100 mL of water
4. customThe methanol was removed in vacuo
5. customthe residue partitioned between water and ethyl acetate
6. extractionThe aqueous phase was extracted with two portions of ethyl acetate
7. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated
10. customto give a yellow solid which
11. customwas used without further purification

ORD record

ord-41d71330e7ae4ec7a4fc2827df44e633

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07238683B2