Potassium Carbonate → 3-Phenylphenol

HRID 2284380Notes

Reaction equation

HRID 2284380 reaction equation
Br[C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O>[C:2]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[C:4]([OH:8])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 115633-BromophenolHCID 66827Phenylboronic Acid

Product 1

HCID 113813-Phenylphenol

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

3-Bromophenol (1.0 g, 5.78 mmol), phenylboronic acid (1.4 g, 11.48 mmol), potassium carbonate (2.0 g, 14.47 mmol), and PdCl2(PPh3) (1/200 eq.) were added to a solution of dioxane/H2O (20 mL/5 mL). The resulting solution was refluxed for 16 h. The reaction mixture was then partitioned between Et2O and water, and the aqueous phase was extracted with Et2O. The combined organic layer was evaporated to dryness and purified by flash column chromatography (ethyl acetate/hexanes=1/9) to give TC-IV-119 (1.02 g, 100%) as a transparent oil.

Workup

  1. temperatureThe resulting solution was refluxed for 16 h
  2. customThe reaction mixture was then partitioned between Et2O and water
  3. extractionthe aqueous phase was extracted with Et2O
  4. customThe combined organic layer was evaporated to dryness
  5. custompurified by flash column chromatography (ethyl acetate/hexanes=1/9)
  6. customto give TC-IV-119 (1.02 g, 100%) as a transparent oil

Sources & evidence

ORD record
ord-082e9d3c14a34016b5e852591b4cc644
Source dataset
uspto-grants-2015_09
Patent number
US09145424B2

Reaction notes

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