Nitric Acid → HCID 118143211, compound

HRID 523957Notes

Reaction equation

HRID 523957 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]2[O:6][C:7]([F:10])([F:9])[O:8][C:4]=2[C:3]=1[Cl:13].[N+:14]([O-])([OH:16])=[O:15]>S(=O)(=O)(O)O>[N+:14]([C:12]1[C:2]([Br:1])=[C:3]([Cl:13])[C:4]2[O:8][C:7]([F:10])([F:9])[O:6][C:5]=2[CH:11]=1)([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 90413817HCID 90413817, compound

Product 1

HCID 118143211HCID 118143211, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
-10 °C

Procedure

The solution of 5-bromo-4-chloro-2,2-diflouro-1,3-benzodioxole (1.5 g, 5.53 mmol) in 10 mL conc. sulfuric acid was cooled to −10° C. Then a solution of 1 mL fuming nitric acid and 2 mL of conc. sulfuric acid was added drop wise. The resulting solution was stirred at −10° C. for ˜2 h. Then the reaction mixture was poured into ice water and a yellow solid precipitated out. Filtered off the solid, rinsed with water and collected the solid. The crude solid was purified by flash chromatography (SiO2, 0-5% ethyl acetate in hexanes) to afford pure 6-nitro-5-bromo-4-chloro-2,2-diflouro-1,3-benzodioxole (1.0 g, 3.16 mmol, 57%). MS: (ES) m/z calculated for C7HBrClF2NO4 [M+H]+ 316.0. found 316.

Workup

  1. customa yellow solid precipitated out
  2. filtrationFiltered off the solid
  3. washrinsed with water
  4. customcollected the solid
  5. customThe crude solid was purified by flash chromatography (SiO2, 0-5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-292f8e7dd0fd4ff485941750d2d555d8
Source dataset
uspto-grants-2016_05
Patent number
US09340509B2

Reaction notes

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