2-Bromo-5-fluorotoluene → 1-Bromo-4-fluoro-2-methyl-5-nitrobenzene
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH3:9].F[B-](F)(F)F.[O:15]=[N+:16]=[O:17]>ClCCl>[Br:1][C:2]1[CH:7]=[C:6]([N+:16]([O-:17])=[O:15])[C:5]([F:8])=[CH:4][C:3]=1[CH3:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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.