Water → HCID 53415539, compound

HRID 271113Notes

Reaction equation

HRID 271113 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH:5]=[CH:6][CH:7]=1.C([O-])(O)=[O:17].[Na+].[O-]S([O-])(=O)=O.[Mg+2].[Mn]([O-])(=O)(=O)=O.[K+].[OH2:33]>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:17])[C:9]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[O:33])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 962WaterHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516875Potassium PermanganateHCID 516892Sodium BicarbonateHCID 598345694-[(3-Bromophenyl)ethynyl]pyridine

Product 1

HCID 53415539HCID 53415539, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-[(3-bromophenyl)ethynyl]pyridine (1.81 g, 7.0 mmol) in acetone (63 mL) is added a warm (˜40° C.) solution of NaHCO3 (0.35 g, 4.20 mmol) and MgSO4 (1.26 g, 10.50 mmol) in H2O (63 mL) followed by the addition of solid potassium permanganate (2.43 g, 15.40 mmol) in one portion. After stirring at room temperature for 4 minutes, the reaction mixture is extracted with 1/1 Et2O/hexane. The extracts are combined, dried over MgSO4 and concentrated to dryness to afford the title compound (1.52 g, 75%) as a solid. Mp: 88-90° C. MS (+) ES: 289 (M+H)+.

Workup

  1. extractionthe reaction mixture is extracted with 1/1 Et2O/hexane
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d22a83343bec4204b1b002ed6c4b7e53
Source dataset
uspto-grants-2008_11
Patent number
US07452885B2

Reaction notes

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