4-Aminophenol → 4-(3-Bromopyridin-2-yloxy)benzenamine

HRID 227771Notes

Reaction equation

HRID 227771 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[CH:6][CH:7]=1.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(C)=O>O>[Br:1][C:2]1[C:3]([O:16][C:13]2[CH:14]=[CH:15][C:10]([NH2:9])=[CH:11][CH:12]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 4034-AminophenolHCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 6933243-Bromo-2-chloropyridine

Product 1

HCID 577562564-(3-Bromopyridin-2-yloxy)benzenamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Bromo-2-chloropyridine (10.3 g, 53.4 mmol), 4-aminophenol (7.00 g, 64.1 mmol), cesium carbonate (34.8 g, 107 mmol), and DMSO (53 ml, 53.4 mmol) were added into a sealed tube. The tube was capped and placed in a preheated oil bath at 130° C. After 16 h, LC-MS showed mainly product. While the reaction mixture was stirring and cooling in ice-water, water was added to induce the product to precipitate out of the solution. A gray solid was obtained, washed with water, dried under vacuum at rt. MS m/z=265 [M+1]+. Calcd for C11H9BrN2O: 263.99.

Workup

  1. customThe tube was capped
  2. customplaced in a preheated oil bath at 130° C
  3. customto precipitate out of the solution
  4. customA gray solid was obtained
  5. washwashed with water
  6. customdried under vacuum at rt

Sources & evidence

ORD record
ord-ae5a045af12b492e849ff6acec777c8a
Source dataset
uspto-grants-2009_07
Patent number
US07560551B2

Reaction notes

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