Chlorotrimethylsilane → HCID 86612587, compound

HRID 646655Notes

Reaction equation

HRID 646655 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[CH:5][C:6]3[C:11]([CH:12]=2)=[CH:10][C:9](Br)=[CH:8][CH:7]=3)[CH:3]=1.C([Li])CCC.CCCCCC.[CH3:28][Si:29](Cl)([CH3:31])[CH3:30]>O.C1(C)C=CC=CC=1.O1CCCC1>[CH3:28][Si:29]([CH3:31])([CH3:30])[C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[CH:5][C:6]3[C:11]([CH:12]=2)=[CH:10][C:9]([Si:29]([CH3:31])([CH3:30])[CH3:28])=[CH:8][CH:7]=3)[CH:3]=1

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8058HexaneHCID 220589062,6-DibromoanthraceneHCID 178418339Butyllithium

Product 1

HCID 86612587HCID 86612587, compoundYield 57%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under an atmospheric argon gas flow, 2,6-dibromoanthracene in an amount of 2.8 g (8.3 millimole), dried tetrahydrofuran (THF) in an amount of 200 milliliter and dried toluene in an amount of 200 milliliter were placed into a three necked-flask equipped with a cooling pipe and having a capacity of 1 liter and then, the resultant solution was cooled down to −30° C. Subsequently, n-butyllithium in an amount of 12 milliliter (19.1 millimole, 1.58 M hexane solution) was added slowly. Then, after adding trimethylsilylchloride in an amount of 2.4 milliliter (19.1 millimole, d=0.85) at a temperature of −70° C., the resultant solution was stirred at a room temperature for 1 hour. After completing the reaction, 100 milliliter of water was added and an organic layer was separated. The solution was dried with a use of sodium sulfate and then, the solvent was separated by distillation, and the residue was washed with a use of 100 milliliter of methanol and as a result, 1.7 g of pale yellow powder was obtained (the yield: 57%).

Workup

  1. customequipped with a cooling pipe
  2. additionwas added
  3. customan organic layer was separated
  4. dry with materialThe solution was dried with a use of sodium sulfate
  5. customthe solvent was separated by distillation
  6. washthe residue was washed with a use of 100 milliliter of methanol and as a result

Sources & evidence

ORD record
ord-bd1257f30b844eb2a8c606737553d1da
Source dataset
uspto-grants-2010_04
Patent number
US07705183B2

Reaction notes

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