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Sodium Carbonate → 2-(3-Furanyl)-4,6-dimethylphenol

HRID 63370
Notes
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Reaction equation

HRID 63370 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][C:13](B(O)O)=[CH:12]1.C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])O.[Na+]>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]>[O:11]1[CH:15]=[CH:14][C:13]([C:2]2[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=2[OH:10])=[CH:12]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 2999762-Bromo-4,6-dimethylphenolHCID 516892Sodium BicarbonateHCID 2734358Furan-3-boronic acid

Product 1

HCID 900027862-(3-Furanyl)-4,6-dimethylphenolYield 54%

Reagents, catalysts & solvents 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

2-Bromo-4,6-dimethylphenol (1.8 g, 8.9 mmol) was dissolved in dimethoxyethane/water (2:1). Furan-3-ylboronic acid (1 g, 8.9 mmol), Pd(dppf)Cl2 (0.36 g, 0.45 mmol) and sodium carbonate (3.7 g, 45 mmol) were added thereto, followed by stirring for 1 hour under reflux. After the completion of the reaction, the reaction mixture was added with a saturated sodium hydrogen carbonate aqueous solution, 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-(furan-3-yl)-4,6-dimethylphenol (0.9 g, 54%).

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-538299e6fa57496392fcca39dcb9cf07
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09447083B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes