Reacción #91660

ord-e11e3cccab8549bbbce0fc5348802ad4

Ecuación de reacción

COc1ccc(O)c(Br)c1
2-Bromo-4-methoxyphenol
OB(O)c1ccco1
2-furanylboronic acid
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
O
water
COc1ccc(O)c(-c2ccco2)c1
2-(furan-2-yl)-4-methoxyphenol
Rendimiento 57.0%

Disolventes

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 (hexane:ethyl acetate=9:1)

Procedimiento

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%).

Fuente

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