2-Bromo-5-fluorotoluene → 1-Bromo-4-fluoro-2-methyl-5-nitrobenzene

To a stirred solution of 1-bromo-4-fluoro-2-methyl-benzene (15.0 g, 79.8 mmol) in dichloromethane (300 mL) was added nitronium tetrafluoroborate (11.7 g, 87.8 mmol) in portions at 0° C. The mixture was heated at reflux for 5 h and was then poured into ice water. The organic layer was separated and the aqueous phase was extracted with dichloromethane (100 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under reduced pressure to give crude 1-bromo-4-fluoro-2-methyl-5-nitrobenzene (18.0 g), which was used directly in the next step.

1. temperatureThe mixture was heated
2. temperatureat reflux for 5 h
3. customThe organic layer was separated
4. extractionthe aqueous phase was extracted with dichloromethane (100 mL×3)
5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
6. customevaporated under reduced pressure

ORD record

ord-ebdb4a4f930d45d5ad488e675eeaa94a

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08846753B2