Reacción #1880953

ord-cdff3a1fbdba4acca673281e345dd166

Ecuación de reacción

Oc1csc(C(F)(F)F)c1
4-hydroxy-2-trifluoromethylthiophene
Fc1cccc(F)n1
2,6-difluoropyridine
CN(C)C=O
DMF
O=C([O-])[O-].[K+].[K+]
K2CO3
Fc1cccc(Oc2csc(C(F)(F)F)c2)n1
2-fluoro-6-(2-trifluoromethyl-4-thienyloxy)pyridine
Rendimiento 74.3%

Disolventes

Condiciones de reacción

Temperatura
80°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturacooled to RT
  2. 2
    ExtracciónAfter extraction twice with heptane/ethyl acetate (1:1)
  3. 3
    Lavadotwice with ethyl acetate the product is washed with water and saturated sodium chloride solution
  4. 4
    Secadodried over MgSO4
  5. 5
    Concentraciónconcentrated
  6. 6
    OtroChromatographic purification on silica gel with heptane/ethyl acetate (3:7) as eluent

Procedimiento

1.00 g of 2,6-difluoropyridine is introduced into 10 ml of DMF under nitrogen and 1.44 g of K2CO3 are added at RT. 1.61 g of 4-hydroxy-2-trifluoromethylthiophene are added and the mixture is heated at 80° C. for 4 h, then cooled to RT and poured into water. After extraction twice with heptane/ethyl acetate (1:1) and twice with ethyl acetate the product is washed with water and saturated sodium chloride solution, dried over MgSO4 and concentrated. Chromatographic purification on silica gel with heptane/ethyl acetate (3:7) as eluent gives 1.7 g of 2-fluoro-6-(2-trifluoromethyl-4-thienyloxy)pyridine as a colorless oil.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07022650B2uspto-grants-2006_04