Tributyltin Chloride → (1-Benzothiophen-3-yl)(tributyl)stannane

HRID 1197425Notes

Reaction equation

HRID 1197425 reaction equation
Br[C:2]1[C:3]2[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=2[S:5][CH:6]=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].[Cl-].[NH4+]>C1COCC1>[S:5]1[CH:6]=[C:2]([Sn:20]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:16][CH2:17][CH2:18][CH3:19])[C:3]2[CH:10]=[CH:9][CH:8]=[CH:7][C:4]1=2

Participants

6

Reactant 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 123250Benzo(b)thiophene, 3-bromo-HCID 178418339Butyllithium

Product 1

HCID 21908239(1-Benzothiophen-3-yl)(tributyl)stannane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

32.0 9 (150 mmol) of 3-bromo-benzo[b]thiophene are added dropwise at -78° C. to a solution of 150 mmol of n-butyllithium in 500 ml of anhydrous THF. The mixture is stirred at -78° C. for 1 h, 52.1 g (160 mmol) of tri-n-butyl-tin chloride are added and the mixture is allowed to warm to room temperature. For working-up, saturated ammonium chloride solution is added and the mixture is extracted with ether. After chromatography on silica gel using petroleum ether, 14.8 g (23 % of theory) of the title compound are obtained.

Workup

  1. temperatureto warm to room temperature
  2. extractionthe mixture is extracted with ether
  3. customare obtained

Sources & evidence

ORD record
ord-77efe45b0577402abee5578fe977f344
Source dataset
uspto-grants-1994_01
Patent number
US05276024

Reaction notes

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