Reacción #63578

Ecuación de reacción

hydrochloric acid

aluminium chloride

1,3-isobenzofurandione

fluorobenzene

→

2-(4-fluorobenzoyl)benzoic acid

Rendimiento 80.7%

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaUpon completion, the whole was heated slowly
2. 2
   Temperaturato reflux
3. 3
   Temperaturaat reflux temperature
4. 4
   TemperaturaThe reaction mixture was cooled
5. 5
   ExtracciónThe product was extracted twice with dichloromethane
6. 6
   LavadoThe combined extracts were washed with a sodium hydroxide solution 10%
7. 7
   OtroThe aqueous phase was separated
8. 8
   Lavadowashed with 2,2'-oxybispropane
9. 9
   Temperaturawhile cooling
10. 10
    workup.STIRRINGThe whole was stirred for one hour at room temperature
11. 11
    FiltraciónThe precipitated product was filtered off
12. 12
    workup.DISSOLUTIONdissolved in benzene
13. 13
    workup.DISTILLATIONThe solution was distilled azeotropically
14. 14
    Otroto dry
15. 15
    workup.STIRRINGThe solid residue was stirred in hexane
16. 16
    FiltraciónThe product was filtered off
17. 17
    Otrodried in vacuo at about 50° C.

Procedimiento

To a stirred mixture of 25 parts of 1,3-isobenzofurandione and 108.5 parts of fluorobenzene were added portionwise 50 parts of aluminium chloride. Upon completion, the whole was heated slowly to reflux and stirring was continued for 1.50 hours at reflux temperature. The reaction mixture was cooled and poured onto a mixture of crushed ice and 60 parts of concentrated hydrochloric acid. The product was extracted twice with dichloromethane. The combined extracts were washed with a sodium hydroxide solution 10%. The aqueous phase was separated, washed with 2,2'-oxybispropane and acidified with concentrated hydrochloric acid while cooling. The whole was stirred for one hour at room temperature. The precipitated product was filtered off and dissolved in benzene. The solution was distilled azeotropically to dry. The solid residue was stirred in hexane. The product was filtered off and dried in vacuo at about 50° C., yielding 33.5 parts (80.7%) of 2-(4-fluorobenzoyl)benzoic acid; mp. 129.2° C. (intermediate 7).

Fuente