Nitric Acid → 5-Nitro-2-(2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole

HRID 343830Notes

Reaction equation

HRID 343830 reaction equation
[F:1][C:2]([F:18])([F:17])[CH2:3][C:4]1([C:13]([F:16])([F:15])[F:14])[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5]1.[N+:19]([O-])([OH:21])=[O:20].S(=O)(=O)(O)O>C(Cl)Cl>[N+:19]([C:11]1[CH:10]=[CH:9][C:7]2[O:8][C:4]([CH2:3][C:2]([F:1])([F:17])[F:18])([C:13]([F:15])([F:14])[F:16])[O:5][C:6]=2[CH:12]=1)([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 536673032-(2,2,2-Trifluoroethyl)-2-(trifluoromethyl)-1,3-benzodioxole

Product 1

HCID 538772305-Nitro-2-(2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 54.4 g of 2-(2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole in 75 ml of methylene chloride was added dropwise at 10° C. to a mixture of 40 ml of 65% strength by weight nitric acid and 40 ml of concentrated sulphuric acid. Stirring was continued for 1 hour at room temperature and the batch was then poured into ice-water, the organic phase was separated off, and the aqueous phase was extracted using methylene chloride. The combined organic phases were washed with water, dried and freed from volatile components. 95 g of the product (=86% of theory), which had a melting point of 87° to 88° C., remained. The NMR spectra showed the following characteristic absorptions: 19F-NMR: -59.0 and -69.4 ppm. 1H-NMR: 3.10 ppm.

Workup

  1. customthe organic phase was separated off
  2. extractionthe aqueous phase was extracted
  3. washThe combined organic phases were washed with water
  4. customdried

Sources & evidence

ORD record
ord-ae0adfc5fd8f4d49b07e6aa955b71d90
Source dataset
uspto-grants-1999_01
Patent number
US05863933

Reaction notes

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