Phenol → HCID 86721028, compound

HRID 930847Notes

Reaction equation

HRID 930847 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:8][C:9]1[C:10](Cl)=[N:11][CH:12]=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[Br:8][C:9]1[C:10]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:11][CH:12]=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 2308893-Bromo-2-chloro-5-nitropyridine

Product 1

HCID 86721028HCID 86721028, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

Phenol (0.416 g, 4.42 mmol), 3-bromo-2-chloro-5-nitropyridine (Combi-Blocks, CAS [5470-17-7], 1 g, 4.21 mmol) and cesium carbonate (1.372 g, 4.21 mmol) were combined in DMSO (8 mL) and heated at 80° C. for 30 minutes. The reaction mixture was cooled and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated. Purification of the residue by chromatography (silica gel, 0-30% ethyl acetate in hexanes) afforded the title compound (1.13 g, 91%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by chromatography (silica gel, 0-30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-d1dbb8891b904f67b76e42a90492a33d
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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