Water → 4-(3-Furanyl)-2,6-dimethylphenol

HRID 63373

Reaction equation

HRID 63373 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1.[O:11]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12]1.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.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]>[O:11]1[CH:15]=[CH:14][C:13]([C:2]2[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=2)=[CH:12]1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 169194-Bromo-2,6-dimethylphenolHCID 2734358Furan-3-boronic acid

Product 1

HCID 900025234-(3-Furanyl)-2,6-dimethylphenolYield 68.7%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

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%).

Workup

  1. customAfter the completion of the reaction
  2. filtrationthe reaction mixture was filtered
  3. extractionThe obtained filtrate was extracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. custompurified by column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-2de7987e35f7458f8887fa5fbfa415af
Source dataset
uspto-grants-2016_09
Patent number
US09447083B2

Linked notes

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