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

HRID 1081293Notes

Reaction equation

HRID 1081293 reaction equation
[Cl:1][CH:2]([C:7]1([C:16]([F:19])([F:18])[F:17])[O:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[O:8]1)[C:3]([F:6])([F:5])[F:4].[N+:20]([O-])([OH:22])=[O:21].S(=O)(=O)(O)O>C(Cl)Cl>[N+:20]([C:13]1[CH:14]=[CH:15][C:9]2[O:8][C:7]([CH:2]([Cl:1])[C:3]([F:6])([F:5])[F:4])([C:16]([F:19])([F:18])[F:17])[O:11][C:10]=2[CH:12]=1)([O-:22])=[O:21]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 544550482-(1-Chloro-2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

613 g of 2-(1-chloro-2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole from Example 2a were dissolved in 1.2 l of methylene chloride, and the solution was added dropwise at 0° to 10° C. to a mixture of 400 ml of 65% strength nitric acid and 400 ml of concentrated sulphuric acid. The mixture was stirred for a further 2 hours at room temperature. It was then carefully placed in 2 l of ice-water and extracted with methylene chloride. The combined organic phases were washed 2 times with water, dried and concentrated. The yield was 652 g (93% of theory). The NMR spectra showed the following characteristic absorptions: 19F-NMR: -66.4 and -79.2 ppm; 1H-NMR: 4.81 ppm.

Workup

  1. extractionextracted with methylene chloride
  2. washThe combined organic phases were washed 2 times with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2b0c1a40e8f044efb92d9b07e99036d4
Source dataset
uspto-grants-1996_12
Patent number
US05585395

Reaction notes

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