1,4-Dibromobenzene → (4-Bromophenyl)tributylstannane

HRID 571438Notes

Reaction equation

HRID 571438 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[Li]CCCC.[Sn:14](Cl)([CH2:23][CH2:24][CH2:25][CH3:26])([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH2:17][CH3:18]>C1COCC1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([Sn:14]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:15][CH2:16][CH2:17][CH3:18])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 78041,4-DibromobenzeneHCID 15096Tributyltin ChlorideHCID 178418339Butyllithium

Product 1

HCID 15695365(4-Bromophenyl)tributylstannaneYield 81.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To p-dibromobenzene (932 mg, 4.00 mmol, 1.00 equiv) in THF (10 mL) at −78° C. was added nBuLi (2.5 M in hexane, 1.6 mL, 4.0 mmol, 1.0 equiv). The reaction mixture was stirred at −78° C. for 30 min before the addition of nBu3SnCl (1.30 g, 4.00 mmol, 1.00 equiv). After stirring for 1.0 hr at −78° C., the reaction mixture was warmed to 23° C. and the solvent was removed in vacuo. the residue was purified by fractional distillation to afford 1.45 g of the title compound as a colorless oil (81% yield).

Workup

  1. temperaturethe reaction mixture was warmed to 23° C.
  2. customthe solvent was removed in vacuo
  3. distillationthe residue was purified by fractional distillation

Sources & evidence

ORD record
ord-110ad166816f4b8f9a5fe5627e407e0f
Source dataset
uspto-grants-2015_05
Patent number
US09024093B2

Reaction notes

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