Nitric Acid → 2-(1-Chloro-2,2,2-trifluoroethyl)-5,6-dinitro-2-(trifluoromethyl)-1,3-benzodioxole

HRID 37574Notes

Reaction equation

HRID 37574 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]2[O:8][C:9]([CH:15]([Cl:20])[C:16]([F:19])([F:18])[F:17])([C:11]([F:14])([F:13])[F:12])[O:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].[N+:23]([O-])([OH:25])=[O:24]>S(=O)(=O)(O)O>[N+:23]([C:22]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]2[O:10][C:9]([CH:15]([Cl:20])[C:16]([F:19])([F:17])[F:18])([C:11]([F:12])([F:13])[F:14])[O:8][C:7]=2[CH:21]=1)([O-:25])=[O:24]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 545213925-Nitro-2-(1-chloro-2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxol

Product 1

HCID 536605592-(1-Chloro-2,2,2-trifluoroethyl)-5,6-dinitro-2-(trifluoromethyl)-1,3-benzodioxole

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
60 °C

Procedure

352 g of 5-nitro-2-(1-chloro-2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole from Example 28 were taken and a mixture of 250 ml of 100% by weight nitric acid and 350 ml of concentrated sulphuric acid was added. The reaction mixture was stirred for 2 hours at 60° C. After cooling, it was poured into ice-water and extracted with methylene chloride. After washing with sodium hydrogencarbonate solution and drying, the extract was concentrated on a rotary evaporator. The yield was 392 g (91% of theory) and the melting point was 125° C. The NMR spectra showed the following characteristic absorptions: 19F NMR: -68.5 and -81.0 ppm. 1H NMR: 4.86 ppm.

Workup

  1. additionwas added
  2. temperatureAfter cooling
  3. extractionextracted with methylene chloride
  4. washAfter washing with sodium hydrogencarbonate solution
  5. customdrying
  6. concentrationthe extract was concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-cc174fb6cf8f4235b2c553b0a1083c78
Source dataset
uspto-grants-1995_05
Patent number
US05420309

Reaction notes

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