Nitric Acid → Methyl 2-bromo-4-fluoro-5-nitrophenoxyformate

HRID 619885Notes

Reaction equation

HRID 619885 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

HCID 944Nitric AcidHCID 13268177Carbonic acid, 2-bromo-4-fluorophenyl methyl ester

Product 1

HCID 13268178Methyl 2-bromo-4-fluoro-5-nitrophenoxyformateYield 92.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

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.

Workup

  1. additionUpon complete addition
  2. washwas washed into the ice-water with 750 mL of water
  3. filtrationThe resultant solid was collected by filtration
  4. washwashed with 1000 mL of water
  5. customThe solid was dried
  6. temperaturewith mild heat under reduced pressure

Sources & evidence

ORD record
ord-da56b96ee9b14929af58d018cd463f7a
Source dataset
uspto-grants-1989_04
Patent number
US04818276

Reaction notes

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