Sodium Carbonate → 2-(3-Furanyl)-6-methylphenol

HRID 63377Notes

Reaction equation

HRID 63377 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].[O:10]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11]1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.O>[O:10]1[CH:14]=[CH:13][C:12]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=2[OH:9])=[CH:11]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2734358Furan-3-boronic acidHCID 110953292-Bromo-6-methylphenol

Product 1

HCID 121871312-(3-Furanyl)-6-methylphenolYield 36.6%

Reagents, catalysts & solvents 1

HCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

2-Bromo-6-methylphenol (800 mg, 4.28 mmol), 3-furan boronic acid (574 mg, 5.13 mmol), sodium carbonate (1400 mg, 12.8 mmol) and Pd2(dppf)2Cl2 (699 mg, 0.82 mmol) were dissolved in dimethoxyethane/water 10 mL/10 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-3-yl)-6-methylphenol (273 mg, 26%).

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-55e799f7c5b64012aa686c6ce8a522b7
Source dataset
uspto-grants-2016_09
Patent number
US09447083B2

Reaction notes

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