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

HRID 1191904Notes

Reaction equation

HRID 1191904 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+]>C1COCC1>[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 98.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-1-indanone (2.0 g, 9.5 mmol) in THF (20 mL) was added NaBH4 (0.5 g, 12.8 mmol). After stirring at room temperature overnight, the solution was quenched by addition of water. The resulting solution was extracted with EtOAc twice. The combined EtOAc layers were dried over Na2SO4 and concentrated under vacuum to give 2.0 g of the title compound as a solid. MS calculated for C9H9BrO: (M+H)+ 212.9. found 194.9 (M+H-H2O)+ , 197.0 (M+H-H2O)+.

Workup

  1. customthe solution was quenched by addition of water
  2. extractionThe resulting solution was extracted with EtOAc twice
  3. dry with materialThe combined EtOAc layers were dried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-42b13c876f504e53ab6b15e2743a982b
Source dataset
uspto-grants-2014_03
Patent number
US08680104B2

Reaction notes

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