Reacción #91664

ord-806c9ce8c3314d68a408c8e779e4dc1f

Ecuación de reacción

Cc1cc(C)c(O)c(Br)c1
2-Bromo-4,6-dimethylphenol
OB(O)c1ccco1
furan-2-ylboronic acid
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
Cc1cc(C)c(O)c(-c2ccco2)c1
2-(furan-2-yl)-4,6-dimethylphenol
Rendimiento 49.3%

Condiciones de reacción

Temperatura
120°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroAfter the completion of the reaction
  2. 2
    Filtraciónthe reaction mixture was filtered
  3. 3
    workup.ADDITIONThe filtrate was added with water
  4. 4
    Extracciónextracted with ethyl acetate
  5. 5
    SecadoThe obtained organic layer was dried over magnesium sulfate
  6. 6
    Otropurified by column chromatography (ethyl acetate:hexane=1:3)

Procedimiento

2-Bromo-4,6-dimethylphenol (500 mg, 2.49 mmol), furan-2-ylboronic acid (88 mg, 2.99 mmol), sodium carbonate (791 mg, 7.47 mmol) and Pd2(dppf)2Cl2 (406 mg, 0.49 mmol) were dissolved in dimethoxyethane/water 6 mL/3 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-2-yl)-4,6-dimethylphenol (231 mg, 45%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09447083B2uspto-grants-2016_09