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

HRID 2368766Notes

Reaction equation

HRID 2368766 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([OH:11])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 5206955-Bromo-1-indanoneHCID 4311764Sodium borohydride

Product 1

HCID 134862995-bromo-2,3-dihydro-1H-inden-1-olYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Bromo-2,3-dihydro-1H-inden-1-one (210 g, 1000 mmol) was suspended in 1 L methanol, and sodium borohydride (41.6 g, 1100 mmol) was added gradually within about 1 hour with stirring. The solvent was removed at 50° C. under reduced pressure after being stirred for another 1 hour. Ethyl acetate (1 L) was added followed by saturated sodium bicarbonate solution (500 mL). After being stirred for some time, the solution was transferred to a separatory funnel and the aqueous phase was removed. The organic phase was washed with saturated sodium bicarbonate solution twice and with brine twice, dried (magnesium sulfate) and finally concentrated to obtain 198 g (93%) of the subtitle compound.

Workup

  1. customThe solvent was removed at 50° C. under reduced pressure
  2. stirringafter being stirred for another 1 hour
  3. additionEthyl acetate (1 L) was added
  4. stirringAfter being stirred for some time
  5. customthe solution was transferred to a separatory funnel
  6. customthe aqueous phase was removed
  7. washThe organic phase was washed with saturated sodium bicarbonate solution twice
  8. dry with materialwith brine twice, dried (magnesium sulfate)
  9. concentrationfinally concentrated

Sources & evidence

ORD record
ord-8800ef57ba4349ab92b1b51de64793c7
Source dataset
uspto-grants-2014_04
Patent number
US08703771B2

Reaction notes

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