Reacción #66035

ord-0d65275dc5704080bbbbe2b39cde242f

Ecuación de reacción

O
water
c1ccc2c(c1)[nH]c1ccccc12
carbazole
CC(=O)c1ccc(F)cc1
4-fluoroacetophenone
O=C([O-])[O-].[K+].[K+]
K2CO3
CC(=O)c1ccc(-n2c3ccccc3c3ccccc32)cc1
product
CC(=O)c1ccc(-n2c3ccccc3c3ccccc32)cc1
1-(4-Carbazol-9-yl-phenyl)ethanone

Reactivos

Ninguno

Disolventes

Condiciones de reacción

Temperatura
135°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroto afford a precipitate
  2. 2
    Otrowhich is isolated by filtration
  3. 3
    Lavadowashed with water
  4. 4
    OtroThe crude product thus obtained
  5. 5
    Otrois further purified by recrystallization from TBME (tert-butyl methyl ether)

Procedimiento

To carbazole (5.02 g) in DMSO (50 mL) is added 4-fluoroacetophenone (3.45 g) and K2CO3 (10.4 g), and the mixture is stirred at 135° C. overnight. The mixture is poured into water to afford a precipitate, which is isolated by filtration and washed with water. The crude product thus obtained is further purified by recrystallization from TBME (tert-butyl methyl ether), giving the product as a light brown solid. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 2.71 (s, 3H), 7.32 (ddd, 2H), 7.41-7.50 (m, 4H), 7.72 (d, 2H), 8.15 (d, 2H), 8.21 (d, 2H).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08524425B2uspto-grants-2013_09