Tributyltin Chloride → HCID 23290214, compound

HRID 366858Notes

Reaction equation

HRID 366858 reaction equation
C([Li])CCC.[S:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:11]1[S:12][CH:13]=[CH:14][CH:15]=1.[CH2:16]([Sn:20](Cl)([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH3:19]>C1COCC1>[CH2:25]([Sn:20]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:21][CH2:22][CH2:23][CH3:24])[C:7]1([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)[CH2:8][CH:9]=[CH:10][S:6]1)[CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 15096Tributyltin ChlorideHCID 681202,2'-BithiopheneHCID 178418339Butyllithium

Product 1

HCID 23290214HCID 23290214, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

n-Butyllithium (22.0 mL, 55.0 mmol, 2.5 M solution in hexane) was added dropwise at -78° C. to a solution of 2,2'-bithiophene (9.44 g, 56.78 mmol) in anhydrous THF (600 mL) under nitrogen. The solution was stirred for 1 h and warmed to -40° C. Tributylstannyl chloride (17.90 g, 55.00 mmol) was added and the entire solution was finally allowed to warm to room temperature. At room temperature the mixture was filtered using Celite and the solvent was stripped. The organo-tin compound was vacuum dried to give 2-(tributylstannyl)-2,2'-bithiophene, obtained as a dark yellow liquid, yield=99%. MS(EI) m/z (rel int): 456 [(M)+, 18%] and 399 [(M)+ --C4H9, 76%].

Workup

  1. temperatureto warm to room temperature
  2. filtrationAt room temperature the mixture was filtered
  3. customdried

Sources & evidence

ORD record
ord-7856d6a548d0499ab734893ac89f8020
Source dataset
uspto-grants-2000_10
Patent number
US06130339

Reaction notes

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