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

HRID 1081295Notes

Reaction equation

HRID 1081295 reaction equation
[N+:1]([O-:4])([OH:3])=O.[N+:5]([C:8]1[CH:26]=[CH:25][C:11]2[O:12][C:13]([CH:19]([Cl:24])[C:20]([F:23])([F:22])[F:21])([C:15]([F:18])([F:17])[F:16])[O:14][C:10]=2[CH:9]=1)([O-:7])=[O:6]>S(=O)(=O)(O)O>[N+:1]([C:26]1[C:8]([N+:5]([O-:7])=[O:6])=[CH:9][C:10]2[O:14][C:13]([CH:19]([Cl:24])[C:20]([F:21])([F:22])[F:23])([C:15]([F:17])([F:16])[F:18])[O:12][C:11]=2[CH:25]=1)([O-:4])=[O:3]

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

A mixture of 250 ml of 100% strength by weight nitric acid and 350 ml of concentrated sulphuric acid was added to an initial charge of 352 g of 5-nitro-2-(1-chloro-2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole from Example 16a. The mixture was stirred for 2 hours at 60° C. It was cooled, poured into ice-water and extracted with methylene chloride. After washing the mixture with sodium hydrogen carbonate solution and drying it was concentrated on a rotary evaporator. The yield was 392 g (91% of theory), 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 to
  2. temperatureIt was cooled
  3. extractionextracted with methylene chloride
  4. washAfter washing the mixture with sodium hydrogen carbonate solution
  5. customdrying it
  6. concentrationwas concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-42884b34a5ed4c3189331735d87cb172
Source dataset
uspto-grants-1996_12
Patent number
US05585395

Reaction notes

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