Water → 6-Bromo-2,3-dihydro-1H-inden-5-ol

HRID 1642644Notes

Reaction equation

HRID 1642644 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][C:6]([OH:10])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C1C(=O)N([Br:18])C(=O)C1.O>CN(C=O)C>[Br:18][C:7]1[CH:8]=[C:9]2[C:4]([CH2:3][CH2:2][CH2:1]2)=[CH:5][C:6]=1[OH:10]

Participants

5

Reactant 3

HCID 962WaterHCID 151185-IndanolHCID 67184N-bromobutanimide

Product 1

HCID 156453446-Bromo-2,3-dihydro-1H-inden-5-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-indanol (6.32 g, 47 mmol) in DMF (20 mL) is added NBS (8.38 g, 47 mmol) and the mixture is stirred at ambient temperature for 1 h. Water is added and the mixture is then extracted with EtOAc. The organic layer is washed with 1N HCl solution and brine, dried with NaSO4 and concentrated to give the title compound and it is used in the next step without purification.

Workup

  1. extractionthe mixture is then extracted with EtOAc
  2. washThe organic layer is washed with 1N HCl solution and brine
  3. dry with materialdried with NaSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-80e32c6f877440b6b53e04d0a34f7e3b
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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