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

HRID 227828Notes

Reaction equation

HRID 227828 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 pressure tube. The tube was capped and placed in a preheated oil bath at 130° C. After 16 h, the reaction mixture was stirred and cooled in ice-water. Water was added slowly to the mixture and the product precipitated out as a gray solid. The solids were washed with water, dried under vacuum at RT to afford 4-(3-bromopyridin-2-yloxy)benzenamine. MS Calcd for C11H9BrN2O: [M]+=264. Found [M+H]+=265.

Workup

  1. customThe tube was capped
  2. customplaced in a preheated oil bath at 130° C
  3. customthe product precipitated out as a gray solid
  4. washThe solids were washed with water
  5. customdried under vacuum at RT

Sources & evidence

ORD record
ord-0e85f67198c54cf087454c85c3602191
Source dataset
uspto-grants-2009_07
Patent number
US07560551B2

Reaction notes

Loading…