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

HRID 37571Notes

Reaction equation

HRID 37571 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% by weight nitric acid and 40 ml of concentrated sulphuric acid. The reaction mixture was subsequently stirred for 1 hour at room temperature and then poured into ice-water, the organic phase was separated off and the aqueous phase was extracted with methylene chloride. The combined organic phases were washed with water and dried and the readily volatile components were removed. The residue consisted of 95 g of product (=86% of theory) melting at 87° to 88° C. 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 with methylene chloride
  3. washThe combined organic phases were washed with water
  4. customdried
  5. customthe readily volatile components were removed

Sources & evidence

ORD record
ord-754b151bb638445b839b3d20944ac26e
Source dataset
uspto-grants-1995_05
Patent number
US05420309

Reaction notes

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