Reacción #68681

ord-3bb0d38912764b8badcae15269f3cc36

Ecuación de reacción

CC1(C)c2ccccc2-c2ccc(Br)cc21
2-bromo-9,9-dimethyl-9H-fluorene
O=C1OC(=O)c2ccccc21
phthalic anhydride
[Al+3].[Cl-].[Cl-].[Cl-]
aluminum chloride
CC1(C)c2cc(Br)ccc2-c2ccc(C(=O)c3ccccc3C(=O)O)cc21
2-(7-bromo-9,9-dimethyl-9H-fluorene-2-carbonyl)benzoic acid
Rendimiento 82.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroAfter the reaction was terminated
  2. 2
    workup.DISTILLATIONdistilled water
  3. 3
    workup.ADDITIONwas gradually added
  4. 4
    Extracciónthe reaction solution was extracted with dichloromethane and 3 times
  5. 5
    Lavadowashed with distilled water
  6. 6
    OtroAfter solvent removal
  7. 7
    workup.ADDITION)-containing vessel
  8. 8
    Lavadowashed
  9. 9
    Filtraciónfiltered
  10. 10
    Otrodried

Procedimiento

2-bromo-9,9-dimethyl-9H-fluorene (40 g, 0.146 mol) and phthalic anhydride (23.8 g, 0.161 mol) were placed in a reaction vessel and dichloromethane (1 l) was added thereto. Then, aluminum chloride (29.2 g, 0.219 mol) was gradually added at 0° C., and the reaction mixture was stirred at room temperature for 12 hours. After the reaction was terminated, distilled water was gradually added, and the reaction solution was extracted with dichloromethane and 3 times washed with distilled water. After solvent removal, the resultant solid was placed in a hexane(2 l)-containing vessel, washed, filtered and dried to give 2-(7-bromo-9,9-dimethyl-9H-fluorene-2-carbonyl)benzoic acid (50.4 g, yield 82%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08525158B2uspto-grants-2013_09