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

HRID 2090752Notes

Reaction equation

HRID 2090752 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-db350fd54eed43e39736f65ec56d80f2
Source dataset
uspto-grants-2013_05
Patent number
US08436187B2

Reaction notes

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