4-Bromophenol → Phenol, 4-(3-pyridinyl)-

HRID 393533Notes

Reaction equation

HRID 393533 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[N:9]1[CH:14]=[CH:13][CH:12]=[C:11](B(O)O)[CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acid

Product 1

HCID 153040Phenol, 4-(3-pyridinyl)-Yield 32.1%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Tetrakis(triphenylphosphine)palladium (139 mg, 0.12 mmol) was added to a flask containing 4-bromophenol (519 mg, 3.0 mmol), 3-pyridyl boronic acid (553 mg, 4.5 mmol) and sodium carbonate (1.27 g, 12.0 mmol). The flask was flushed with nitrogen and ethanol (6 mL) and water (0.6 mL) were added. The mixture was placed in an oil bath at 80° C. for 16 h. Upon cooling to RT the mixture was partitioned between water and chloroform. The aqueous layer was extracted with chloroform (3×) and the combined organic layers were dried (Na2SO4), filtered and concentrated. The crude residue was purified by chromatography (Biotage, 40S) eluting with 50% ethyl acetate in hexanes to afford 165 mg (32%) of 4-pyridin-3-yl-phenol as a white solid: mp=194.6° C., MS (Cl) m/z 172.1 (M+1).

Workup

  1. customThe flask was flushed with nitrogen and ethanol (6 mL) and water (0.6 mL)
  2. additionwere added
  3. customwas partitioned between water and chloroform
  4. extractionThe aqueous layer was extracted with chloroform (3×)
  5. dry with materialthe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by chromatography (Biotage, 40S)
  9. washeluting with 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-5173c04914e1483eac24562ccc144ec8
Source dataset
uspto-grants-2004_10
Patent number
US06809094B2

Reaction notes

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