Water → 2-(Tri-n-butylstannyl)thiophene

HRID 1012524Notes

Reaction equation

HRID 1012524 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.C([Li])CCC.[CH2:12]([Sn:16](Cl)([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH3:15].O>O1CCCC1.CCCCCC>[CH2:21]([Sn:16]([CH2:12][CH2:13][CH2:14][CH3:15])([CH2:17][CH2:18][CH2:19][CH3:20])[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1)[CH2:22][CH2:23][CH3:24]

Participants

7

Reactant 4

HCID 962WaterHCID 138512-BromothiopheneHCID 15096Tributyltin ChlorideHCID 178418339Butyllithium

Product 1

HCID 27793732-(Tri-n-butylstannyl)thiophene

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution (10 mL) of 2-bromothiophene (1.0 g) in tetrahydrofuran was cooled to −70° C., and a 1.6 mol/L solution (4.2 mL) of n-butyllithium in hexane was added dropwise. After stirring at the same temperature for 30 min, tributyltin chloride (2.1 g) was added dropwise. After further stirring for 1 hr, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residual oil (2.4 g) containing the title compound was used for the next step without purification.

Workup

  1. stirringAfter further stirring for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionThe residual oil (2.4 g) containing the title compound
  7. customwas used for the next step without purification

Sources & evidence

ORD record
ord-402e8f6d2e314c0a9e8e3e6f678b69ac
Source dataset
uspto-grants-2011_07
Patent number
US07977488B2

Reaction notes

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