2,2,2-Trifluoroethanol → 4-Chloro-2-nitro-5-(2,2,2-trifluoroethyloxy)toluene

HRID 1747

Reaction equation

HRID 1747 reaction equation
CC([O-])(C)C.[K+].[Cl:7][C:8]1[C:13](Cl)=[CH:12][C:11]([CH3:15])=[C:10]([N+:16]([O-:18])=[O:17])[CH:9]=1.[CH2:19]([OH:24])[C:20]([F:23])([F:22])[F:21]>>[Cl:7][C:8]1[C:13]([O:24][CH2:19][C:20]([F:23])([F:22])[F:21])=[CH:12][C:11]([CH3:15])=[C:10]([N+:16]([O-:18])=[O:17])[CH:9]=1

Participants

4

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 3437951,2-Dichloro-4-methyl-5-nitrobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 196923224-Chloro-2-nitro-5-(2,2,2-trifluoroethyloxy)toluene

Procedure

40.4 g (360 mmol) of potassium tert-butylate were added in portions to 60 ml of trifluoroethanol, while stirring and cooling, and the mixture was heated to 80°-90° C. After cooling, 14.4 g (70 mmol) of 4,5-dichloro-2-nitrotoluene were added and the mixture was stirred at 105° C. for 1 hour. It was concentrated in vacuo and the residue was treated with 300 ml of water to give, after filtration with suction, 12 g of crude product, which were purified over silica gel with n-heptane/ethyl acetate, 10 g of product, melting point 76°-79° C.

Workup

  1. temperaturecooling
  2. temperaturethe mixture was heated to 80°-90° C
  3. temperatureAfter cooling
  4. stirringthe mixture was stirred at 105° C. for 1 hour
  5. concentrationIt was concentrated in vacuo
  6. additionthe residue was treated with 300 ml of water
  7. customto give
  8. filtrationafter filtration with suction, 12 g of crude product, which
  9. customwere purified over silica gel with n-heptane/ethyl acetate, 10 g of product, melting point 76°-79° C.

Sources & evidence

ORD record
ord-5c297b4a87b04776a1276a465dc94abc
Source dataset
uspto-grants-1998_03
Patent number
US05726305

Linked notes

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