1,3-Difluorobenzene → HCID 10813782, compound

HRID 1489425Notes

Reaction equation

HRID 1489425 reaction equation
[F:1][C:2]([F:25])([CH:22]([F:24])[F:23])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15](=[O:16])[N:14]([C@H:17]([CH3:21])[C:18](Cl)=[O:19])[N:13]=[CH:12]2)=[CH:7][CH:6]=1.[Cl-].[Al+3].[Cl-].[Cl-].[F:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=1>ClCCl>[F:30][C:31]1[CH:32]=[C:33]([F:37])[CH:34]=[CH:35][C:36]=1[C:18](=[O:19])[C@H:17]([N:14]1[C:15](=[O:16])[N:11]([C:8]2[CH:9]=[CH:10][C:5]([O:4][CH2:3][C:2]([F:25])([F:1])[CH:22]([F:24])[F:23])=[CH:6][CH:7]=2)[CH:12]=[N:13]1)[CH3:21]

Participants

5

Reactant 3

HCID 97411,3-DifluorobenzeneHCID 6451240Aluminum(III) ChlorideHCID 10786113HCID 10786113, compound

Product 1

HCID 10813782HCID 10813782, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2R)-2-[4-[4-(2,2,3,3-Tetrafluoropropoxy)phenyl]-4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl]propanoyl chloride (1 g) was dissolved in 20 ml of dichloromethane, to which 2.5 ml of 1,3-difluorobenzene and 1.50 g of anhydrous aluminium chloride in a powdery form were added. The mixture was refluxed with heating for eight hours. After cooling, the reaction solution was poured into 50 ml of ice water and extracted from a mixture of 100 ml of ethyl acetate and 50 ml of diisopropyl ether. The extract was washed with 30 ml of 1N-hydrochloric acid and 30 ml of a saturated aqueous solution of sodium chloride successively, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (silica gel: 60 g, eluent; hexane:ethyl acetate:acetic acid=2:1:0.03) to give 0.77 g of 2-[(1R)-2-(2,4-difluorophenyl)-2-oxo-1-methylethyl]-4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-3(2H,4H)-1,2,4-triazolone (yield: 61%) as a pale yellow oil.

Workup

  1. additionwere added
  2. temperatureThe mixture was refluxed
  3. temperaturewith heating for eight hours
  4. temperatureAfter cooling
  5. extractionextracted from a mixture of 100 ml of ethyl acetate and 50 ml of diisopropyl ether
  6. washThe extract was washed with 30 ml of 1N-hydrochloric acid and 30 ml of a saturated aqueous solution of sodium chloride successively
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel chromatography (silica gel: 60 g, eluent; hexane:ethyl acetate:acetic acid=2:1:0.03)

Sources & evidence

ORD record
ord-62ae63067fe54c9eac6a85eaf54a0f1a
Source dataset
uspto-grants-1997_10
Patent number
US05677464

Reaction notes

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