Nitric Acid → 1,2-Difluoro-4-nitrobenzene

Temperature

-12 °C

This material is prepared as described by R. W. Taft, G. B. Klingensmith, and S. Ehrenson (J. Am. Chem. Soc., 87, 3620 (1965)). To a stirred mixture of 5.0 ml of concentrated nitric acid and 13.9 ml of concentrated sulfuric acid cooled to -12° C. is added 9.7 g (0.085 mole) of 1,2-difluorobenzene. A slight exotherm is observed and the mixture is cooled to -20° C. whereupon it solidifies. The mixture is stirred for forty-five minutes at -5° to 0° and is then allowed to warm slowly to room temperature. After one hour the mixture is poured onto ice, and the mixture extracted with diethyl ether (3×75 ml). The combined ether extracts are washed with water, 10% aqueous Na2CO3, and water again. The ether solution is dried (MgSO4) and concentrated in vacuo without external heating to give the crude product (11.9 g), which is distilled (kugelrohr apparatus) to give 10.2 g of colorless liquid. The nmr spectrum of this material is consistent with the structure.

1. customThis material is prepared
2. temperaturethe mixture is cooled to -20° C. whereupon it
3. temperatureto warm slowly to room temperature
4. additionAfter one hour the mixture is poured onto ice
5. extractionthe mixture extracted with diethyl ether (3×75 ml)
6. washThe combined ether extracts are washed with water, 10% aqueous Na2CO3, and water again
7. dry with materialThe ether solution is dried (MgSO4)
8. concentrationconcentrated in vacuo
9. temperaturewithout external heating
10. customto give the crude product (11.9 g), which
11. distillationis distilled (kugelrohr apparatus)

ORD record

ord-9f2a41c117b148a597f3b0cbd8f94821

Source dataset

uspto-grants-1980_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04200588