Sodium Carbonate → 2-(2-Furanyl)-4,6-dimethylphenol

HRID 63386

Reaction equation

HRID 63386 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.O>[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2999762-Bromo-4,6-dimethylphenolHCID 2734357Furan-2-boronic acid

Product 1

HCID 900027952-(2-Furanyl)-4,6-dimethylphenolYield 49.3%

Reagents, catalysts & solvents 1

HCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

2-Bromo-4,6-dimethylphenol (500 mg, 2.49 mmol), furan-2-ylboronic acid (88 mg, 2.99 mmol), sodium carbonate (791 mg, 7.47 mmol) and Pd2(dppf)2Cl2 (406 mg, 0.49 mmol) were dissolved in dimethoxyethane/water 6 mL/3 mL, followed by stirring in microwave at 120° C. for 20 minutes. After the completion of the reaction, the reaction mixture was filtered using Celite. The filtrate was added with water, and extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, and purified by column chromatography (ethyl acetate:hexane=1:3) to obtain 2-(furan-2-yl)-4,6-dimethylphenol (231 mg, 45%).

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe reaction mixture was filtered
  3. additionThe filtrate was added with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe obtained organic layer was dried over magnesium sulfate
  6. custompurified by column chromatography (ethyl acetate:hexane=1:3)

Sources & evidence

ORD record
ord-806c9ce8c3314d68a408c8e779e4dc1f
Source dataset
uspto-grants-2016_09
Patent number
US09447083B2

Linked notes

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