Water → 2,4-Dimethyl-6-(3-pyridinyl)phenol

HRID 63375

Reaction equation

HRID 63375 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[N:11]1[CH:16]=[CH:15][CH:14]=[C:13](B(O)O)[CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C(COC)OC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([C:13]2[CH:12]=[N:11][CH:16]=[CH:15][CH:14]=2)[C:3]=1[OH:10]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2999762-Bromo-4,6-dimethylphenolHCID 27343783-Pyridinylboronic acid

Product 1

HCID 900024552,4-Dimethyl-6-(3-pyridinyl)phenolYield 70.3%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

2-bromo-4,6-dimethylphenol (1 g, 5 mmol) was dissolved in dimethoxyethane/water (2:1). Pyridin-3-ylboronic acid (0.62 g, 5 mmol) and Pd(dppf)Cl2 (0.20 g, 0.25 mmol), sodium carbonate (2.1 g, 25 mmol) were added thereto, followed by stirring for 1 hour under reflux. After the completion of the reaction, the reaction mixture was added with water, and extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, concentrated under reduced pressure, and purified by column chromatography to obtain 2,4-dimethyl-6-(pyridin-3-yl)phenol (0.7 g, 70%).

Workup

  1. temperatureunder reflux
  2. customAfter the completion of the reaction
  3. extractionextracted with ethyl acetate
  4. dry with materialThe obtained organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-d1d0cdab6b9e420f8018c3c663768b30
Source dataset
uspto-grants-2016_09
Patent number
US09447083B2

Linked notes

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