Chlorotrimethylsilane → 3,5-Dibromo-1-trimethylsilylbenzene

HRID 2282794Notes

Reaction equation

HRID 2282794 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](Br)[CH:5]=[C:4]([Br:9])[CH:3]=1.O1CCCC1.C([Li])CCC.Cl[Si:21]([CH3:24])([CH3:23])[CH3:22]>CO.C(N(CC)CC)C>[Br:1][C:2]1[CH:7]=[C:6]([Si:21]([CH3:24])([CH3:23])[CH3:22])[CH:5]=[C:4]([Br:9])[CH:3]=1

Participants

7

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8028TetrahydrofuranHCID 122791,3,5-TribromobenzeneHCID 178418339Butyllithium

Product 1

HCID 6262443,5-Dibromo-1-trimethylsilylbenzene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

1 g of 1,3,5-tribromobenzene was added to 20 mL of tetrahydrofuran and the temperature was adjusted to −78° C. Subsequently, 1.65 mL of butyllithium was slowly added dropwise. The mixture was stirred for 2 hr while maintaining its temperature, and 0.45 g of chlorotrimethylsilane was slowly added dropwise, after which the temperature of the mixture was raised to room temperature. After completion of the reaction, triethylamine and methanol were added, and the reaction mixture was stirred and extracted, followed by drying the solvent. The resulting solid was filtered and purified, yielding (3,5-dibromophenyl)trimethylsilane as an intermediate.

Workup

  1. customwas adjusted to −78° C
  2. additionwas slowly added dropwise
  3. additionwere added
  4. stirringthe reaction mixture was stirred
  5. extractionextracted
  6. customby drying the solvent
  7. filtrationThe resulting solid was filtered
  8. custompurified

Sources & evidence

ORD record
ord-8f156dde4f2d41e2b2b6d2728d8f2c08
Source dataset
uspto-grants-2015_09
Patent number
US09142784B2

Reaction notes

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