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

HRID 374846Notes

Reaction equation

HRID 374846 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 to a mixture of 40 ml of 65% strength by weight nitric acid and 40 ml of concentrated sulphuric acid at i0° C. The mixture was subsequently stirred at room temperature for 1 hour and then poured onto 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, dried and freed from readily volatile constituents. 95 g of the product (=86% of theory) with a melting point of 87° to 88° C. remained.

Workup

  1. additionpoured onto ice-water
  2. customthe organic phase was separated off
  3. extractionthe aqueous phase was extracted with methylene chloride
  4. washThe combined organic phases were washed with water
  5. customdried

Sources & evidence

ORD record
ord-40e89fa1aee2452d830837edebfe73df
Source dataset
uspto-grants-1996_01
Patent number
US05482956

Reaction notes

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