Hydrochloric Acid → 4-Bromo-2,3-dihydro-1H-inden-1-ol

HRID 234078

Reaction equation

HRID 234078 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].[BH4-].[Na+].Cl>C(O)C.O1CCCC1>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][CH:6]2[OH:11]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 987131-Indanone, 4-bromo-HCID 4311764Sodium borohydride

Product 1

HCID 133302084-Bromo-2,3-dihydro-1H-inden-1-ol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-1-indanone (1.0 g) in a mixture of ethanol (6 ml) and tetrahydrofuran (3 ml) was added sodium borohydride (0.09 g) at an ice temperature. The reaction mixture was stirred at the same temperature overnight and poured into dilute hydrochloric acid, and the aqueous layer was saturated with saline and extracted with ether. The organic layer was washed with a saturated aqueous saline, dried over sodium sulfate, and the solvent was removed by distillation under reduced pressure. The residual concentrate (1.02 g) thus obtained was used for the next reaction without further purification.

Workup

  1. extractionextracted with ether
  2. washThe organic layer was washed with a saturated aqueous saline
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was removed by distillation under reduced pressure
  5. concentrationThe residual concentrate (1.02 g)
  6. customthus obtained
  7. customwas used for the next reaction without further purification

Sources & evidence

ORD record
ord-01f71f65fdf84ea39e9ca101f8c5f389
Source dataset
uspto-grants-1997_01
Patent number
US05594081

Linked notes

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