Water → 2-(Furan-2-yl)-4-methoxyphenol

HRID 63382Notes

Reaction equation

HRID 63382 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][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+].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][CH:13]=[C:12]1[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[OH:10]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2973822-Bromo-4-methoxyphenolHCID 2734357Furan-2-boronic acid

Product 1

HCID 900024462-(Furan-2-yl)-4-methoxyphenolYield 57%

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

2-Bromo-4-methoxyphenol (400 mg, 1.97 mmol), 2-furanylboronic acid (287 mg, 2.56 mmol), Pd(dppf)Cl2 (81 mg, 0.1 mmol) and sodium carbonate (626 mg, 5.91 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 filtrate was added with water, and extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, and purified by column chromatography (hexane:ethyl acetate=9:1) to obtain 2-(furan-2-yl)-4-methoxyphenol (212 mg, 57%).

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 (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-e11e3cccab8549bbbce0fc5348802ad4
Source dataset
uspto-grants-2016_09
Patent number
US09447083B2

Reaction notes

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