Iodine → Trimethyl(M-tolyl)silane

HRID 1735181Notes

Reaction equation

HRID 1735181 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1.Cl[Si:10]([CH3:13])([CH3:12])[CH3:11].[Mg].II.[Cl-].[NH4+]>CCOCC>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Si:10]([CH3:13])([CH3:12])[CH3:11])[CH:3]=1

Participants

7

Reactant 5

HCID 807IodineHCID 6397ChlorotrimethylsilaneHCID 115603-BromotolueneHCID 25517Ammonium ChlorideHCID 5462224Magnesium

Product 1

HCID 10866684Trimethyl(M-tolyl)silaneYield 53.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 9.2 g (50 mmol) of 3-bromo-toluene and 5.84 g (50 mmol) of chlorotrimethylsilane in 100 ml of dry ether are added dropwise to 1.2 g (50 mmol) of magnesium turnings in a few milliliters of ether, some crystals of iodine are added to start the reaction. The reaction mixture is refluxed for 20 hours after the end of the addition and then poured into a saturated solution of ammonium chloride (200 ml). The aqueous solution is further extracted with ether, the ethereal extracts are combined, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford 4.4 g of a yellowish liquid. Flash chromatography ona silica gel column and elution with petroleum ether give 2.3 g (30%) of the expected 1-methyl-3-trimethylsilyl-benzene as a colorless liquid.

Workup

  1. customthe reaction
  2. temperatureThe reaction mixture is refluxed for 20 hours
  3. additionafter the end of the addition
  4. extractionThe aqueous solution is further extracted with ether
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5711752a6cbf4be6a68052cf30282f49
Source dataset
uspto-grants-1996_07
Patent number
US05536732

Reaction notes

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