Benzene, 1-bromo-2-(trifluoromethyl)- → Stannane, tributyl[2-(trifluoromethyl)phenyl]-

HRID 440756Notes

Reaction equation

HRID 440756 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([F:11])([F:10])[F:9].C([Li])CCC.[CH2:17]([Sn:21](Cl)([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:19][CH3:20]>O1CCCC1>[CH2:26]([Sn:21]([CH2:17][CH2:18][CH2:19][CH3:20])([CH2:22][CH2:23][CH2:24][CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([F:11])([F:10])[F:9])[CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 9806Benzene, 1-bromo-2-(trifluoromethyl)-HCID 15096Tributyltin ChlorideHCID 178418339Butyllithium

Product 1

HCID 11015608Stannane, tributyl[2-(trifluoromethyl)phenyl]-Yield 86.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 10.0 g of 2-bromotrifluoromethylbenzene under nitrogen in 100 ml of tetrahydrofuran while cooling in a dry ice-acetone bath is added dropwise 30.6 ml of a 1.6M solution of butyl lithium via syringe. Stirring is continued for 1 hour. To the reaction mixture is added dropwise 15.9 g of tributyltin chloride in 30 ml of tetrahydrofuran. Stirred ? additional hours. The reaction mixture is quenched with 20 ml of water and after stirring for 20 minutes, extracted with chloroform (3×100 ml). The organic layer is filtered through diatomaceous earth and the filtrate washed with saturated NaHCO3 and water. The organic layer is dried (Na2SO4) and evaporated in vacuo to give 16.8 g of the desired product. MS 379.1

Workup

  1. stirringStirred
  2. customThe reaction mixture is quenched with 20 ml of water
  3. stirringafter stirring for 20 minutes
  4. extractionextracted with chloroform (3×100 ml)
  5. filtrationThe organic layer is filtered through diatomaceous earth
  6. washthe filtrate washed with saturated NaHCO3 and water
  7. dry with materialThe organic layer is dried (Na2SO4)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-567bce7754dd465ca6a969c62a8b56f4
Source dataset
uspto-grants-1996_05
Patent number
US05521173

Reaction notes

Loading…