2-Chloro-6-fluorotoluene → 2-Chloro-4-fluoro-3-methyl-1-nitrobenzene

1-Chloro-3-fluoro-2-methylbenzene (1.00 mL, 8.24 mmol) was dissolved in sulfuric acid (18 M, 10 mL) and cooled in an ice bath. Potassium nitrate (0.87 g, 8.65 mmol) dissolved in sulfuric acid (18 M, 10 mL) was added dropwise to the cold solution. The reaction mixture was stirred for 5 min, then the ice bath was removed and stirring was continued for another 2 h. The reaction mixture was poured onto ice (25 g) stirred for 5 min and extracted with ethyl acetate (3×25 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated to give a clear yellow oil (1.34 g, purity 85%). The product was used without further purification in the next reaction step.

1. temperaturecooled in an ice bath
2. additionwas added dropwise to the cold solution
3. customthe ice bath was removed
4. stirringstirring
5. waitwas continued for another 2 h
6. additionThe reaction mixture was poured onto ice (25 g)
7. stirringstirred for 5 min
8. extractionextracted with ethyl acetate (3×25 mL)
9. dry with materialThe combined organic layers were dried over sodium sulfate
10. filtrationfiltered
11. customevaporated
12. customto give a clear yellow oil (1.34 g, purity 85%)
13. customThe product was used without further purification in the next reaction step

ORD record

ord-6511610d5fc746328c28928cbeaa3cac

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07585877B2