5-Nitro-2-(1-chloro-2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxol → HCID 54242850, compound

HRID 37579Notes

Reaction equation

HRID 37579 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]2[O:8][C:9]([CH:15]([Cl:20])[C:16]([F:19])([F:18])[F:17])([C:11]([F:14])([F:13])[F:12])[O:10][C:6]=2[CH:5]=1)([O-])=O>O1CCCC1.[H][H].[Pd]>[NH2:1][C:4]1[CH:22]=[CH:21][C:7]2[O:8][C:9]([CH:15]([Cl:20])[C:16]([F:19])([F:17])[F:18])([C:11]([F:12])([F:13])[F:14])[O:10][C:6]=2[CH:5]=1

Participants

5

Reactant 1

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

Product 1

HCID 54242850HCID 54242850, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

72 g of 5-nitro-2-(1-chloro-2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole from Example 28 were dissolved in 500 ml of tetrahydrofuran and hydrogenated with 15-20 bar of hydrogen for 5 hours at room temperature on 5 g of palladium-on-charcoal (5%). The mixture was then filtered and the solvent was stripped off under vacuum. The yield was 60 g (93% of theory) and the boiling point was 80°-82° C. at 0.1 mbar. The NMR spectra showed the following characteristic absorptions: 19F NMR: -66.5 and -79.4 ppm. 1H NMR: 4.68 ppm.

Workup

  1. filtrationThe mixture was then filtered

Sources & evidence

ORD record
ord-9e6d8444a22c4076bf452ed69feee895
Source dataset
uspto-grants-1995_05
Patent number
US05420309

Reaction notes

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