Water → 104473-58-7

HRID 1596058Notes

Reaction equation

HRID 1596058 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][O:25]C(=O)C.O>CN(C=O)C.CCOC(C)=O.CO>[OH:25][CH2:24][CH2:23][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium Carbonate2×HCID 135641-Acetoxy-2-bromoethaneHCID 1406104'-Hydroxy-4-biphenylcarbonitrile

Product 1

HCID 13879371104473-58-7Yield 78%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 4′-hydroxy-4-biphenylcarbonitrile (1.014 g, 5.19 mmol) in 10 mL DMF was added potassium carbonate (2.15 g, 15.6 mmol, 3 eq.) and 2-bromoethylacetate. After two hours at 50° C., the reaction mixture was cooled to room temperature, diluted with 50 mL EtOAc, washed with H2O (3×10 mL), dried (Na2SO4), filtered, and concentrated to provide a white solid. The solid was dissolved in 20 mL MeOH and 5 mL H2O and potassium carbonate (2.15 g, 15.6 mmol) were added. After 30 minutes, the MeOH was evaporated and the crude reaction was taken up in EtOAc and washed with H2O (10 mL×3), dried (Na2SO4), filtered, concentrated, and purified on silica gel to provide 0.967g (78%) of the desired compound.

Workup

  1. washwashed with H2O (3×10 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto provide a white solid
  6. waitAfter 30 minutes
  7. customthe MeOH was evaporated
  8. customthe crude reaction
  9. washwashed with H2O (10 mL×3)
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. concentrationconcentrated
  13. custompurified on silica gel

Sources & evidence

ORD record
ord-71d20abe8a5643c2baad264764f4c583
Source dataset
uspto-grants-2001_09
Patent number
US06288261B1

Reaction notes

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