Reaction #91651

Reaction equation

4-Bromo-2,6-dimethylphenol

3-furanylboronic acid

sodium carbonate

water

→

4-(furan-3-yl)-2,6-dimethylphenol

Yield 68.7%

Solvents

DME

Conditions

Workup

1. 1
   OtherAfter the completion of the reaction
2. 2
   Filtrationthe reaction mixture was filtered
3. 3
   ExtractionThe obtained filtrate was extracted with ethyl acetate
4. 4
   Dryingdried over magnesium sulfate
5. 5
   Otherpurified by column chromatography (hexane:ethyl acetate=9:1)

Procedure

4-Bromo-2,6-dimethylphenol (350 mg, 1.74 mmol), 3-furanylboronic acid (269 mg, 2.26 mmol), Pd(dppf)Cl2 (71 mg, 0.087 mmol) and sodium carbonate (553 mg, 5.22 mmol) were dissolved in DME:water=4 mL:2 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 obtained filtrate was extracted with ethyl acetate, dried over magnesium sulfate, and purified by column chromatography (hexane:ethyl acetate=9:1) to obtain 4-(furan-3-yl)-2,6-dimethylphenol (225 mg, 50%).

Source