Dichloromethane → HCID 71059442, compound

HRID 1425593Notes

Reaction equation

HRID 1425593 reaction equation
C(Cl)Cl.CC1(C)C(C)(C)OB([C:12]2[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=2)O1.Cl[C:21]1[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][CH:24]=[CH:23][N:22]=1.C(=O)([O-])[O-].[K+].[K+]>O.[Cu]I>[N+:27]([C:26]1[C:21]([C:12]2[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=2)=[N:22][CH:23]=[CH:24][CH:25]=1)([O-:29])=[O:28]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 796132-Chloro-3-nitropyridineHCID 27346233-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Product 1

HCID 71059442HCID 71059442, compoundYield 48.9%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent

Procedure

[1,1′-Bis(diphenylphosphino)ferrocnee]dichloropalladium(II), w/DCM (0.039 g, 0.047 mmol) was added to a solution containing 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (0.292 g, 1.325 mmol), 2-chloro-3-nitropyridine (0.15 g, 0.946 mmol), Copper(I) iodide (0.018 g, 0.095 mmol) and Potassium carbonate (0.946 ml, 1.892 mmol). Heated the reaction to 110° C. for 15 mins. Cooled reaction to room temperature. Diluted with water and extracted with ethyl acetate. Combined organics, dried, filtered, concentrated and purified to afford 3-(3-nitropyridin-2-yl)phenol (0.1 g, 0.463 mmol, 48.9% yield).

Workup

  1. additionwas added to a solution
  2. temperatureHeated
  3. customthe reaction to 110° C. for 15 mins
  4. temperatureCooled
  5. customreaction to room temperature
  6. extractionextracted with ethyl acetate
  7. customCombined organics, dried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified

Sources & evidence

ORD record
ord-9707b75576bd4175a14e45329b910e25
Source dataset
uspto-grants-2015_01
Patent number
US08932557B2

Reaction notes

Loading…