Water → HCID 68670309, compound

HRID 2071041Notes

Reaction equation

HRID 2071041 reaction equation
Br[C:2]1[CH:3]=[C:4]([OH:12])[CH:5]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:7]=1.[C:13]([Cu])#[N:14].C(OCC)(=O)C.O>CN(C=O)C>[C:8]([C:6]1[CH:7]=[C:2]([CH:3]=[C:4]([OH:12])[CH:5]=1)[C:13]#[N:14])([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 578373843-tert-butyl-5-bromophenolHCID 178418546HCID 178418546, compound2×

Product 1

HCID 68670309HCID 68670309, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
170 °C

Procedure

A solution of 403 mg of 3-bromo-5-tert-butylphenol and 200 mg (1.28 mmol) of CuCN in 5 mL of DMF was stirred at 160° C. After 75 min. 365 mg of CuCN was added and stirring was continued at 160° C. After about 1 h, the temperature was increased to 170° C. and the mixture was refluxed for 19 h. Ethyl acetate and H2O were added, and the mixture was filtered through a Buchner funnel, and the layers were separated. The organic layer was washed with 10 mL of H2O and brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (15% EtOAc/hexanes) provided 153 mg of 3-tert-butyl-5-hydroxybenzonitrile as an orange solid in 49% yield.

Workup

  1. customwas continued at 160° C
  2. waitAfter about 1 h
  3. temperaturethe mixture was refluxed for 19 h
  4. filtrationthe mixture was filtered through a Buchner funnel
  5. customthe layers were separated
  6. washThe organic layer was washed with 10 mL of H2O and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by flash silica gel chromatography (15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-f593cf28f2ba4535b2346bc263e6e150
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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