4-Iodophenol → 4-(4-Methylphenyl)phenol

HRID 899501Notes

Reaction equation

HRID 899501 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.[OH-].[Na+]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=2)=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 108944-IodophenolHCID 14798Sodium HydroxideHCID 79799Tolylboronic acid

Product 1

HCID 13827894-(4-Methylphenyl)phenolYield 48%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×

Procedure

Palladium(II) acetate (52 mg, 0.23 mmol) was added to a mixture of 4-iodophenol (5.00 g, 22.7 mmol), 4-methyl-phenyl-boronic acid (3.4 g, 25.0 mmol), sodium hydroxide (3.6 g, 90 mmol), and water (9 mL). The mixture was diluted twice with water (9 mL) to facilitate stirring. An exotherm occurred, and after 15 minutes the internal temperature was 50° C. The reaction mixture was cooled to room temperature and allowed to stir overnight, and the solid was filtered off, washed with water, and dissolved in ethyl acetate. The organic solution was washed with water, three times with 1 M NaOH, and then again with water until the washings were neutral. The solution was then dried (sodium sulfate), filtered, and evaporated to give 4′-methyl-biphenyl-4-ol (2 g, 48%).

Workup

  1. stirringto stir overnight
  2. filtrationthe solid was filtered off
  3. washwashed with water
  4. dissolutiondissolved in ethyl acetate
  5. washThe organic solution was washed with water, three times with 1 M NaOH
  6. dry with materialThe solution was then dried (sodium sulfate)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-8ba68155e4364a0ab51d4fcb9bd0a56e
Source dataset
uspto-grants-2008_04
Patent number
US07355049B2

Reaction notes

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