Reacción #1178403

ord-872db2b33d2542f090ee8bc0c2fb14aa

Ecuación de reacción

O=C(Cc1ccccc1)Cc1ccccc1
1,3-Diphenylacetone
O=C1C(=O)c2ccc(Br)c3cccc1c23
5-bromoacenaphthenequinone
[K+].[OH-]
KOH
O=C1C(c2ccccc2)=C2C(=C1c1ccccc1)c1ccc(Br)c3cccc2c13
3-Bromo-7,9-diphenyl-8H-Cyclopent[a]acenaphthylen-8-one

Disolventes

Condiciones de reacción

Temperatura
65°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otroprecipitated immediately
  2. 2
    workup.STIRRINGThe mixture was then stirred at 65° C. for 1 hour
  3. 3
    Temperaturacooled
  4. 4
    Filtraciónfiltered
  5. 5
    LavadoThe black solid was washed well with methanol, ether
  6. 6
    Otrodried

Procedimiento

1,3-Diphenylacetone (17.5 g, 83 mMole) was dissolved in methanol (240 mL) and heated to 65° C. To the solution was added 5-bromoacenaphthenequinone (2), (20 g, 75 mMole). The resulting well-stirred suspension was then treated with 1M-methanolic KOH (100 ML, 100 mMole) at a fast drip rate, whereupon the dark colored product precipitated immediately. The mixture was then stirred at 65° C. for 1 hour, cooled and filtered. The black solid was washed well with methanol, ether and dried. Yield of product (3), (31 g).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08129039B2uspto-grants-2012_03