Sulfuric acid magnesium salt (1:1) → 3-Bromothieno(3,2-c)pyridine

HRID 226066Notes

Reaction equation

HRID 226066 reaction equation
[S:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][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.C(Cl)(Cl)Cl>[Br:28][C:3]1[C:4]2[CH:5]=[N:6][CH:7]=[CH:8][C:9]=2[S:1][CH:2]=1

Participants

9

Reactant 5

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 24408BromineHCID 24450Potassium Phosphate, DibasicHCID 67500Thieno(3,2-c)pyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 6120393-Bromothieno(3,2-c)pyridineYield 29%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

1.46 g of Thieno[3,2-c]pyridine (10.8 mmol), 907 mg of NaHCO3 (10.8 mmol), 2.82 g of K2HPO4 (16.2 mmol) and 1.69 g of MgSO4 (14.04 mmol) are placed into the flask with 40 ml of chloroform. The reaction mixture is stirred under reflux. 0.72 ml of bromine (14.04 mmol) is added slowly to the mixture and kept stirring for overnight. CH2Cl2 and water are added to the cooled reaction mixture and separated CH2Cl2 layer is dried over Na2SO4 and evaporated. The crude product is applied onto a silica-gel chromatography column (Hexane: AcOEt=5:1→Hexane:AcOEt:2 M NH3 in MeOH=10:3:1) to give 660 mg of the title compound. Yield 29%. mass spectrum (m/e): 215 (M+1); 1H-NMR (CDCl3): 9.17 (m, 1H), 8.59 (m, 1H), 7.83 (d, 1H, J=5.2 Hz), 7.52 (s, 1H) ppm.

Workup

  1. temperatureunder reflux
  2. stirringkept stirring for overnight
  3. customseparated CH2Cl2 layer
  4. dry with materialis dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-826559024927418893aad0e22dd775ae
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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