Sodium Carbonate → 4,7-Di(thiophen-2-yl)benzo(c)(1,2,5)thiadiazole

HRID 881780

Reaktionsgleichung

Reaktionsgleichung von HRID 881780
Br[C:2]1[C:10]2[C:6](=[N:7][S:8][N:9]=2)[C:5](Br)=[CH:4][CH:3]=1.[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[S:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[C:2]1[C:10]2[C:6](=[N:7][S:8][N:9]=2)[C:5]([C:13]2[S:12][CH:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 6263614,7-Dibromo-2,1,3-benzothiadiazoleHCID 27339602-Thiopheneboronic acid

Produkt 1

HCID 3962944,7-Di(thiophen-2-yl)benzo(c)(1,2,5)thiadiazole

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A solution of 4,7-dibromobenzo[c][1,2,5]thiadiazole (3.0 g, 10.2 mmol) and thiophen-2-ylboronic acid (2.87 g, 22.4 mmol) in 150 mL of 1,2-dimethoxyethane and 50 mL anhydrous ethanol was carefully degassed by bubbling nitrogen through the solution. Next, 7.16 g (67.2 mmol) of sodium carbonate dissolved in 30 mL water was added. The resulting emulsion was degas sed, and the catalyst Pd(PPh3)4 (200 mg, 0.17 mmol) was added. Afterwards, the mixture was refluxed under nitrogen overnight. After removal of the organic solvent by reduced pressure, the mixture was poured into water (300 mL) and was extracted with chloroform (3×40 mL). The organic phase was washed with water (30 mL), dried over magnesium sulphate, and the solvent was removed in vacuo. Purification by flash silica gel column chromatography [hexane:chloroform=1:1 (v/v)] followed by recrystallization from hexane/dichloromethane (DCM) yielded orange crystals of TBT (2.6 g, 84.9%).

Aufarbeitung

  1. customby bubbling nitrogen through the solution
  2. additionwas added
  3. customThe resulting emulsion was degas sed
  4. temperatureAfterwards, the mixture was refluxed under nitrogen overnight
  5. customAfter removal of the organic solvent by reduced pressure
  6. additionthe mixture was poured into water (300 mL)
  7. extractionwas extracted with chloroform (3×40 mL)
  8. washThe organic phase was washed with water (30 mL)
  9. dry with materialdried over magnesium sulphate
  10. customthe solvent was removed in vacuo
  11. customPurification by flash silica gel column chromatography [hexane:chloroform=1:1 (v/v)]
  12. customfollowed by recrystallization from hexane/dichloromethane (DCM)
  13. customyielded orange crystals of TBT (2.6 g, 84.9%)

Quellen und Nachweise

ORD-Eintrag
ord-56a7ee08aeeb4f2fa1a7d2a991458e63
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993697B2

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