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

HRID 1639664Notes

Reaction equation

HRID 1639664 reaction equation
[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=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>C(Cl)(Cl)Cl.O>[Br:28][C:3]1[C:4]2=[N:5][CH:6]=[CH:7][CH:8]=[C:9]2[S:1][CH:2]=1

Participants

8

Reactant 5

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 24408Bromine2×HCID 24450Potassium Phosphate, DibasicHCID 516892Sodium BicarbonateHCID 12210218Thienopyridine

Product 1

HCID 132204283-Bromothieno[3,2-b]pyridineYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

Combine thieno[3,2-b]pyridine (3.45 g, 25.6 mmol), sodium bicarbonate (2.15 g, 25.6 mmol), K2HPO4 (6.69 g, 38.4 mmol) and MgSO4 (4.01 g, 33.3 mmol) in CHCl3 (60 mL). Stir the mixture under reflux and add Br2 (1.57 mL, 30.7 mmol) slowly. Stir the reaction mixture under reflux overnight. Add more bromine (0.7 mL) and stir the reaction under reflux for 4 h. Cool to room temperature, add water, and extract with CHCl3. Wash the organic portion with saturated Na2S2O3 solution and saturated brine. Dry over Na2SO4 and evaporate. Recrystallize the material from hexane/CH2Cl2 to obtain the title compound (3.94 g, 72%). ES/MS m/z (81Br) 215 (M+).

Workup

  1. temperatureunder reflux
  2. stirringStir the reaction mixture
  3. temperatureunder reflux overnight
  4. stirringstir
  5. customthe reaction
  6. temperatureunder reflux for 4 h
  7. extractionextract with CHCl3
  8. washWash the organic portion with saturated Na2S2O3 solution and saturated brine
  9. dry with materialDry over Na2SO4
  10. customevaporate
  11. customRecrystallize the material from hexane/CH2Cl2

Sources & evidence

ORD record
ord-4005c5700efa4dff9f3d6582d51951a2
Source dataset
uspto-grants-2012_02
Patent number
US08110580B2

Reaction notes

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