Sulfuric acid magnesium salt (1:1) → 3-Bromothieno[2,3-b]pyridine

HRID 226069

Reaktionsgleichung

Reaktionsgleichung von HRID 226069
[S:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.C([O-])(O)=O.[Na+].OP([O-])([O-])=O.[K+].[K+].[O-]S([O-])(=O)=O.[Mg+2].[Br:28]Br>O.C(Cl)Cl>[Br:28][C:3]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[S:1][CH:2]=1

Komponenten

8

Edukt 5

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 24408BromineHCID 24450Potassium Phosphate, DibasicHCID 289928Thieno(2,3-b)pyridineHCID 516892Sodium Bicarbonate

Produkt 1

HCID 2899263-Bromothieno[2,3-b]pyridineAusbeute 48,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

2.30 g of Thieno[2,3-b]pyridine (17 mmol), 1.43 g of NaHCO3 (17 mmol), 4.44 g of K2HPO4 (25.5 mmol) and 2.66 g of MgSO4 (22.1 mmol) are placed into the flask with 80 ml of dichloromethane. The reaction mixture is stirred under reflux. 1.05 ml of bromine (20.4 mmol) is added slowly to the mixture and is stirred overnight. CH2Cl2 and water are added to the cooled reaction mixture and separated. The CH2Cl2 layer is dried over Na2SO4 and evaporated. The crude product is applied onto a silica-gel chromatography column (Hexane: AcOEt=3:1) to give 1.76 g of the title compound. Yield 48%. mass spectrum (m/e): 215 (M+1); 1H-NMR (CDCl3): 8.67 (m, 1H), 8.13 (m, 1H), 7.59 (s, 1H), 7.45 (m, 1H) ppm.

Aufarbeitung

  1. temperatureunder reflux
  2. stirringis stirred overnight
  3. customseparated
  4. dry with materialThe CH2Cl2 layer is dried over Na2SO4
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-137de9ad09d94fd7bf2c4d32b1346a4c
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557103B2

Verknüpfte Notizen

Wird geladen…