2-(Tri-n-butylstannyl)thiophene → HCID 86674216, compound

HRID 1897399Notes

Reaction equation

HRID 1897399 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)CCC.Br[N:20]1[C:24]2[CH:25]=[C:26]([N+:33]([O-:35])=[O:34])[C:27]([N+:30]([O-:32])=[O:31])=[C:28](Br)[C:23]=2[NH:22][S:21]1>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[S:7]1[CH:8]=[CH:9][CH:10]=[C:6]1[N:20]1[C:24]2[CH:25]=[C:26]([N+:33]([O-:35])=[O:34])[C:27]([N+:30]([O-:32])=[O:31])=[C:28]([C:6]3[S:7][CH:8]=[CH:9][CH:10]=3)[C:23]=2[NH:22][S:21]1

Participants

5

Reactant 2

HCID 27793732-(Tri-n-butylstannyl)thiopheneHCID 86674217HCID 86674217, compound

Product 1

HCID 86674216HCID 86674216, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-Tributylstannylthiophene (9.06 g, 24.3 mmol) and 1,4-dibromo-5,6-dinitro-2,1,3-benzothiadiazole (3.80 g, 9.90 mmol) were dissolved in anhydrous THF (150 mL). After adding Pd(PPh3)2Cl2 (338 mg, 0.48 mmol), reflux was performed for 16 hours. After the reaction was terminated, the temperature was raised to room temperature and the solvent was removed. The product was extracted with dichloromethane and distilled water, dried, subjected to column chromatography (neutral alumina, hexane) and recrystallized in toluene to obtain yellow solid. 1H NMR (500 MHz, CDCl3, ppm): δ 7.75 (dd, 2H, J=5.0 Hz, J=1.0 Hz), 7.52 (dd, 2H, J=3.5 Hz, J=1.0 Hz), 7.24 (dd, 2H, J=5.0 Hz, J=3.5 Hz).

Workup

  1. temperaturereflux
  2. customAfter the reaction was terminated
  3. customthe solvent was removed
  4. extractionThe product was extracted with dichloromethane
  5. distillationdistilled water
  6. customdried
  7. customrecrystallized in toluene
  8. customto obtain yellow solid

Sources & evidence

ORD record
ord-cdc62c06fc464a168bd3c44b233f0681
Source dataset
uspto-grants-2013_08
Patent number
US08519087B2

Reaction notes

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