Tributyltin Chloride → Stannane, [2,2'-bithiophen]-5-yltributyl-

HRID 430733Notes

Reaction equation

HRID 430733 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1.C([Li])CCC.[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:5]1[S:1][C:2]([C:6]2[S:7][CH:8]=[CH:9][CH:10]=2)=[CH:3][CH:4]=1)[CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

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

Product 1

HCID 11201877Stannane, [2,2'-bithiophen]-5-yltributyl-Yield 124.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The synthesis described herein is depicted schematically in FIG. 4. 1.0 g (6 mmol) of bithiophene in 30 ml THF was treated dropwise with 3.54 ml (6 mmol) of 1.70 M n-butyllithium and stiffed for 0.5 h at −78° C. under N2 atmosphere. 1.96 ml of tributylstannyl chloride (7.2 mmol) was then added to the solution. After stirring at room temperature for 6 h, the solvent was evaporated and the residue was dissolved in 20 ml of hexane and filtered. The filtrate was evaporated to produce 3.4 g of crude 5-(tributylstannyl)-2,2-bithiophene as a light yellow liquid for the next step reaction. 1H NMR: (250 MHZ, CDCl3): d (ppm) 7.27 (d, 1H), 7.15 (2d, 2H), 7.03 (d, 1H), 6.98 (t, 1H), 1.54 (m, 6H), 1.31 (m, 6H), 1.10 (t, 6H), 0.89 (m, 9H). 13C NMR (125 MHZ, CDCl3): d (ppm) 136.28, 127.98, 127.94, 125.19, 124.56, 124.17, 123.97, 123.66, 29.10, 27.50, 13.91, 11.11. MS (FAB): (M+) found: 456, calcd for C20H32S2Sn: 455.28.

Workup

  1. customthe solvent was evaporated
  2. dissolutionthe residue was dissolved in 20 ml of hexane
  3. filtrationfiltered
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-78db00d4e1cd4d6dad64e0bb5183c972
Source dataset
uspto-grants-2001_11
Patent number
US06323309B1

Reaction notes

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