2-Bromotoluene → Tributyl(2-methylphenyl)stannane

HRID 440731Notes

Reaction equation

HRID 440731 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8].C([Li])CCC.[CH2:14]([Sn:18](Cl)([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH3:17]>O1CCCC1.CCCCCC>[CH2:23]([Sn:18]([CH2:14][CH2:15][CH2:16][CH3:17])([CH2:19][CH2:20][CH2:21][CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8])[CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 3

HCID 72362-BromotolueneHCID 15096Tributyltin ChlorideHCID 178418339Butyllithium

Product 1

HCID 2737000Tributyl(2-methylphenyl)stannaneYield 92.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To a stirred solution of 3.4 g of 2-bromotoluene in 100 ml of dry tetrahydrofuran at -78° C. is slowly added 8 ml of 2.5M butyl lithium in hexane. The reaction mixture is stirred for 30 minutes and 6.5 g of tri-n-butyl tin chloride in 25 ml of tetrahydrofuran added. The reaction mixture is stirred an additional 1 hour, quenched with water and extracted with ether. The ether extract is dried over Na2SO4, filtered and the filtrate evaporated in vacuo to give 7.0 g of a residue. Mass spectrum: M+H:381.

Workup

  1. customat -78° C.
  2. stirringThe reaction mixture is stirred an additional 1 hour
  3. customquenched with water
  4. extractionextracted with ether
  5. extractionThe ether extract
  6. dry with materialis dried over Na2SO4
  7. filtrationfiltered
  8. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-3fd8c5d348984b9795a537fd2194f9ab
Source dataset
uspto-grants-1996_05
Patent number
US05521173

Reaction notes

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