Nitric Acid → Methyl 2-bromo-4-fluoro-5-nitrophenoxyformate
Reaction equation
[C:1](=[O:13])([O:11][CH3:12])[O:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[Br:10].[N+:14]([O-])([OH:16])=[O:15]>S(=O)(=O)(O)O>[C:1](=[O:13])([O:11][CH3:12])[O:2][C:3]1[CH:8]=[C:7]([N+:14]([O-:16])=[O:15])[C:6]([F:9])=[CH:5][C:4]=1[Br:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A rapidly stirred solution of 946 g (3.8 moles) of 2-bromo-4-fluorophenyl methyl carbonate in 1292 mL of sulfuric acid was cooled to 5°-10° C., and 368 g (4.18 moles) of 70% nitric acid was added dropwise over two hours. Upon complete addition, the reaction mixture was allowed to warm to ambient temperature and was stirred for two hours. The reaction mixture was poured into 5000 mL of ice water. Any material remaining in the reaction vessel was washed into the ice-water with 750 mL of water. The resultant solid was collected by filtration and washed with 1000 mL of water. The solid was dried with mild heat under reduced pressure to give 1031 g of 2-bromo-4-fluoro-5nitrophenyl methyl carbonate.