Triethylamine → 2-(2,2,2-Trifluoroethyl)-2-(trifluoromethyl)-1,3-benzodioxole

HRID 343837Notes

Reaction equation

HRID 343837 reaction equation
Cl[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].C(N(CC)CC)C.[H][H]>C1COCC1.[Pd]>[F:6][C:3]([F:4])([F:5])[CH2:2][C:7]1([C:16]([F:17])([F:19])[F:18])[O:8][C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[O:11]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 544550482-(1-Chloro-2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxoleHCID 178418361HCID 178418361, compound

Product 1

HCID 536673032-(2,2,2-Trifluoroethyl)-2-(trifluoromethyl)-1,3-benzodioxole

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

306.5 g of 2-(1-chloro-2,2,2-trifluoroethyl)-2-trifluoromethyl-1,3-benzodioxole of Example 2a were dissolved in 500 ml of THF and the solution was treated with 101 g of triethylamine and 30 g of palladium on charcoal (5% strength by weight). The mixture was then hydrogenated for 48 hours at 110° C. under 100 bar hydrogen. The mixture was subsequently filtered, the solvent was stripped off, and the residue was subjected to fractionation in vacuo. The yield was 126 g (46% of theory), and the boiling point was 60° C. at 10 mbar. The NMR spectra showed the following characteristic absorptions: 19F-NMR: -59.0 and -84.6 ppm. 1H-NMR: 3.02 ppm.

Workup

  1. filtrationThe mixture was subsequently filtered

Sources & evidence

ORD record
ord-75dca0221bac4fa99264447078d598f7
Source dataset
uspto-grants-1999_01
Patent number
US05863933

Reaction notes

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