Sulfuric Acid → 2-Chloro-4-fluoro-5-nitrotoluene

Temperature

0 °C

To a mixture of 20.0 g (0.138 mole) of 2-chloro-4fluorotoluene in 50 ml of 1,2-dichloroethane which had been cooled to 0° C. was added 50 ml of concentrated sulfuric acid. While maintaining the temperature below 10° C., 14.0 g (0.138 mole) of potassium nitrate was added slowly to the mixture. After three hours the reaction mixture was poured into ice, and the resulting mixture was extracted with methylene chloride. The extract was dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure. The residue was passed through a silica gel column, eluting with heptane. Appropriate fractions were combined, and the solvent was evaporated under reduced pressure, yielding 13.0 g of 2-chloro-4-fluoro-5-nitrotoluene as a yellow solid. The nmr spectrum was consistent with the proposed structure.

1. additionwas added slowly to the mixture
2. additionAfter three hours the reaction mixture was poured into ice
3. extractionthe resulting mixture was extracted with methylene chloride
4. dry with materialThe extract was dried over anhydrous magnesium sulfate
5. filtrationfiltered
6. customthe solvent was evaporated under reduced pressure
7. washeluting with heptane
8. customthe solvent was evaporated under reduced pressure

ORD record

ord-ae2b6f4c832b4099b29069b3827135d1

Source dataset

uspto-grants-1989_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04846882