4-Bromophenol → 3-(4-Hydroxyphenyl)benzonitrile

HRID 1619722Notes

Reaction equation

HRID 1619722 reaction equation
[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1)#[N:2].Br[C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:19][C:16]1[CH:17]=[CH:18][C:13]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 78084-BromophenolHCID 10340Sodium CarbonateHCID 27343253-Cyanophenylboronic acid

Product 1

HCID 37790963-(4-Hydroxyphenyl)benzonitrileYield 44.4%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

3-Cyanophenylboronic acid (1.18 g, 8.03 mmol), 4-bromophenol (1.16 g, 6.69 mmol) and sodium carbonate (2.12 g, 20.07 mmol) were dissolved in dioxane (20 mL) and water (8 mL) and the reaction mixture was degassed under nitrogen. Tetrakistriphenylphosphinepalladium (0) (0.77 g, 0.67 mmol) was added and the reaction was stirred at 110° C. for 2 hours. The mixture was cooled to room temperature, filtered through pad of Arbocel™ and the filtrate was concentrated in vacuo. The residue was partitioned between ethyl acetate (30 mL) and water (15 mL). The organic layer was dried over anhydrous magnesium sulphate, filtered and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with 40% ethyl acetate in heptane to give the title compound as a pale yellow solid (0.58 g, 44%).

Workup

  1. customwater (8 mL) and the reaction mixture was degassed under nitrogen
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered through pad of Arbocel™
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was partitioned between ethyl acetate (30 mL) and water (15 mL)
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated in vacuo
  9. customThe residue was purified by flash chromatography on silica gel eluting with 40% ethyl acetate in heptane

Sources & evidence

ORD record
ord-eba15ac3243d4b91be0c92d5c3e6ed2c
Source dataset
uspto-grants-2014_07
Patent number
US08772293B2

Reaction notes

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