Water → Stannane, trimethyl(4-methylphenyl)-

HRID 578587Notes

Reaction equation

HRID 578587 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.C([Li])CCC.[CH3:14][Sn:15](Cl)([CH3:17])[CH3:16].O>CCOCC>[CH3:14][Sn:15]([CH3:17])([CH3:16])[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78054-BromotolueneHCID 14016Trimethyltin chlorideHCID 178418339Butyllithium

Product 1

HCID 617834Stannane, trimethyl(4-methylphenyl)-Yield 77%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-78 °C

Procedure

100 g (0.585 mol) of 1-bromo-4-methylbenzene was dissolved in 500 mL of anhydrous ether in an argon atmosphere, and then cooled to −78° C. 252 mL (2.5M in hexane, 0.615 mol) of an n-butyl lithium solution was slowly added dropwise. The mixture was stirred for 15 minutes, and a solution of 122.6 g (0.615 mol) of trimethyltin chloride in 500 mL of ether was added. The mixture was stirred for 2 hours while the temperature was gradually increased to room temperature, followed by the addition of 700 mL of distilled water and then stirring. The organic layer was separated, treated with magnesium sulfate, filtered, and concentrated under reduced pressure, yielding trimethyl(p-tolyl)tin as represented below in a 77% yield.

Workup

  1. stirringThe mixture was stirred for 2 hours while the temperature
  2. temperaturewas gradually increased to room temperature
  3. stirringstirring
  4. customThe organic layer was separated
  5. additiontreated with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-31c5657915d44c9c9e761146415f0044
Source dataset
uspto-grants-2015_05
Patent number
US09040572B2

Reaction notes

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