Reacción #2507821

ord-13518cb5df374d488085f5a455bfc6b3

Ecuación de reacción

[H-].[K+]
potassium hydride
CCCC1COc2cc(C(CO)Cc3cc(F)c(Br)cc3F)c(F)cc2C1
3-(4-bromo-2,5-difluorophenyl)-2-(6-fluoro-3-propylchroman-7-yl)propan-1-ol
CCO
ethanol
CCCC1COc2cc(C3COc4cc(Br)c(F)cc4C3)c(F)cc2C1
7-bromo-6,6′-difluoro-3′-propyl-3,4,3′,4′-tetrahydro-2H,2′H-[3,7′]-bichromenyl

Disolventes

Condiciones de reacción

Temperatura
60°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Lavadowashed with sat. sodium chloride soln
  2. 2
    Secadophase is dried over sodium sulfate
  3. 3
    Otrothe solvent is removed in vacuo
  4. 4
    Filtraciónthe crude product is filtered through silica gel with toluene
  5. 5
    Otrorecrystallised from heptane/ethyl acetate

Procedimiento

1.2 g (10.5 mmol) of potassium hydride (35 percent in paraffin oil) are initially introduced in 40 ml of THF, and a solution of 4.50 g (8.12 mmol) of 3-(4-bromo-2,5-difluorophenyl)-2-(6-fluoro-3-propylchroman-7-yl)propan-1-ol in 20 ml of THF is added dropwise at 30° C. The batch is subsequently stirred at 60° C. for 4 h, a little ethanol is added, and the batch is diluted with MTB ether and washed with sat. sodium chloride soln. The org. phase is dried over sodium sulfate, the solvent is removed in vacuo, and the crude product is filtered through silica gel with toluene and recrystallised from heptane/ethyl acetate, giving 7-bromo-6,6′-difluoro-3′-propyl-3,4,3′,4′-tetrahydro-2H,2′H-[3,7′]-bichromenyl as colourless crystals.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07955664B2uspto-grants-2011_06