3-Bromothiophene → Stannane, tributyl-3-thienyl-

HRID 2254453Notes

Reaction equation

HRID 2254453 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][CH:3]=1.[CH2:7]([Sn:11](Cl)([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH2:14][CH3:15])[CH2:8][CH2:9][CH3:10]>C(OCC)C>[CH2:16]([Sn:11]([CH2:7][CH2:8][CH2:9][CH3:10])([CH2:12][CH2:13][CH2:14][CH3:15])[C:2]1[CH:6]=[CH:5][S:4][CH:3]=1)[CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 133833-BromothiopheneHCID 15096Tributyltin Chloride

Product 1

HCID 10959689Stannane, tributyl-3-thienyl-Yield 74.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5 g of 3-bromothiophene was dissolved in 35 ml of anhydrous ethyl ether, and with stirring under cooling at -70° to -65° C., 19 ml of a 15% n-butyllithium-hexane solution and 10.5 g of tributyltin chloride were added. The mixture was stirred at the above temperature for 1 hour and then at room temperature for 1 hour. The reaction mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate, and then the solvent was evaporated. The residue was purified by distillation under reduced pressure to give 8.5 g (yield 74%) of tributyl(3-thienyl)tin, b.p. 150°-158° C./2 mmHg.

Workup

  1. temperatureunder cooling at -70° to -65° C.
  2. stirringThe mixture was stirred at the above temperature for 1 hour
  3. washThe reaction mixture was washed with a saturated aqueous solution of sodium hydrogen carbonate
  4. customthe solvent was evaporated
  5. distillationThe residue was purified by distillation under reduced pressure

Sources & evidence

ORD record
ord-f73bcc72c5394a918283dcd9b738c27d
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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