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

HRID 2084552Notes

Reaction equation

HRID 2084552 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

The compound obtained in Step A (70.19 mmol) is brought into solution in 420 ml of CHCl3, and bromotrimethylsilane (13.90 ml, 105.28 mmol, 1.5 eq.) is added at room temperature. The reaction mixture is stirred overnight at room temperature. The solvent and excess bromotrimethylsilane are removed by evaporation under reduced pressure. The oil is taken up in 150 ml of CHCl3, washed with 2×80 ml of water and 3×100 ml of saturated NaCl and dried over Na2SO4. The organic phase is then concentrated under reduced pressure to yield the title compound in the form of a brown oil.

Workup

  1. customThe solvent and excess bromotrimethylsilane are removed by evaporation under reduced pressure
  2. washwashed with 2×80 ml of water and 3×100 ml of saturated NaCl
  3. dry with materialdried over Na2SO4
  4. concentrationThe organic phase is then concentrated under reduced pressure

Sources & evidence

ORD record
ord-20974b9e15294dafbc8e34a64e6b255b
Source dataset
uspto-grants-2004_04
Patent number
US06716852B2

Reaction notes

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