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

HRID 48492Notes

Reaction equation

HRID 48492 reaction equation
[Br:1][C:2]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:3]=1[O:4][C:5]([O:7][CH3:8])=[O:6].[N+:14]([O-])([OH:16])=[O:15]>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:12]=[C:11]([F:13])[C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:3]=1[O:4][C:5]([O:7][CH3:8])=[O:6]

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 97.7%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

Then, 110 g (0.44 mol) of methyl 2-bromo-4-fluorophenoxyformate was dissolved in 250 ml of sulfuric acid, to which a mixed acid of 30 g of fuming nitric acid and 30 ml of sulfuric acid was added dropwise at 5° C. or lower, and the mixture was stirred for 2 hours. The reaction mixture was poured onto ice, and the precipitated crystals were collected by filtration, washed with water, and dried, which afforded 126 g (0.43 mol) of methyl 2-bromo-4-fluoro-5-nitrophenoxyformate.

Workup

  1. additionwas added dropwise at 5° C.
  2. additionThe reaction mixture was poured onto ice
  3. filtrationthe precipitated crystals were collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-0f13797f74d449c092f060ea899a8952
Source dataset
uspto-grants-2004_03
Patent number
US06703503B2

Reaction notes

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