Bromotrimethylsilane → 1,5-Dibromo-2,3-dihydro-1H-indene

HRID 1292739Notes

Reaction equation

HRID 1292739 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7](O)[CH2:6][CH2:5]2.[Br:12][Si](C)(C)C>C(Cl)(Cl)Cl>[Br:12][CH:7]1[C:8]2[C:4](=[CH:3][C:2]([Br:1])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 134862995-bromo-2,3-dihydro-1H-inden-1-ol

Product 1

HCID 227325721,5-Dibromo-2,3-dihydro-1H-indene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a nitrogen-purged flask was added 100 mg (0.469 mmol) of 5-bromoindan-1-ol from Step A and 3 mL of anhydrous chloroform, followed by 0.096 mL (0.704 mmol) of bromotrimethylsilane. The reaction mixture was stirred at ambient temperature overnight and concentrated. The residue was partitioned between ethyl acetate and water. The organic phase was washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, and concentrated to give a brown oil which was used without further purification. Mass spectrum (MS): m/z 195, 197 (M+1-HBr), 116 (M+1-2HBr).

Workup

  1. customTo a nitrogen-purged flask
  2. concentrationconcentrated
  3. customThe residue was partitioned between ethyl acetate and water
  4. washThe organic phase was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto give a brown oil which
  8. customwas used without further purification

Sources & evidence

ORD record
ord-ec62b51a66dc43eda88977270131fa42
Source dataset
uspto-grants-2007_07
Patent number
US07238683B2

Reaction notes

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