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

HRID 1081297Notes

Reaction equation

HRID 1081297 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.[H][H]>O1CCCC1.[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 2

HCID 545213925-Nitro-2-(1-chloro-2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxolHCID 178418361HCID 178418361, compound

Product 1

HCID 54242850HCID 54242850, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

72 g of 5-nitro-2-(1-chloro-2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole from Example 16a were dissolved in 500 ml of tetrahydrofuran, and hydrogenated using 5 g of palladium on carbon (5%) for 5 hours at room temperature with 15 to 20 bar of hydrogen. The mixture was then filtered and the solvent stripped off in vacuo. The yield was 60 g (93% of theory), the boiling point was 80° to 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. customfor 5 hours
  2. customat room temperature
  3. filtrationThe mixture was then filtered

Sources & evidence

ORD record
ord-e5c07ade2fdc46e695098fe6d4c4a646
Source dataset
uspto-grants-1996_12
Patent number
US05585395

Reaction notes

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