Trimethyltin chloride → Stannane, trimethyl(3-methylphenyl)-

HRID 1655517Notes

Reaction equation

HRID 1655517 reaction equation
[CH3:1][Sn:2](Cl)([CH3:4])[CH3:3].[C:6]1([CH3:14])[CH:11]=[CH:10][C:9]([Mg]Br)=[CH:8][CH:7]=1.[Cl-].[NH4+]>C1COCC1>[CH3:1][Sn:2]([CH3:4])([CH3:3])[C:10]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:14])[CH:11]=1

Participants

5

Reactant 3

HCID 14016Trimethyltin chlorideHCID 25517Ammonium ChlorideHCID 178418370HCID 178418370, compound

Product 1

HCID 617758Stannane, trimethyl(3-methylphenyl)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 21.5 g (100 mmol) trimethyltin chloride in 500 mL THF at -35° C. was added 113 mL (113 mmol) 1.0M p-tolylmagnesium bromide over 3 minutes. The mixture was allowed to warm to RT and stir for 1 hour after which time was added saturated aqueous ammonium chloride. The mixture was extracted three times with ether. The combined organic material was washed with brine, was dried over MgSO4, was stripped of solvent in vacuo, then was distilled at 0.1 Torr with the title compound distilling between 66°-74° C. The bitolyl remaining in the still pot crystallized upon cooling. The title compound was isolated as a clear, shiny liquid, 25.4 (92% yield).

Workup

  1. extractionThe mixture was extracted three times with ether
  2. washThe combined organic material was washed with brine
  3. dry with materialwas dried over MgSO4
  4. distillationwas distilled at 0.1 Torr with the title compound
  5. distillationdistilling between 66°-74° C
  6. customThe bitolyl remaining in the still pot crystallized
  7. temperatureupon cooling

Sources & evidence

ORD record
ord-367d2e8bbb59487095482a6ec03273e7
Source dataset
uspto-grants-1993_10
Patent number
US05250521

Reaction notes

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