1,3-Difluorobenzene → HCID 10527851, compound

HRID 1489431Notes

Reaction equation

HRID 1489431 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[CH:15]=[CH:14][N:13]([C@H:16]([CH3:20])[C:17](Cl)=[O:18])[C:12]2=[O:21])=[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:17](=[O:18])[C@H:16]([N:13]1[CH:14]=[CH:15][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)[C:12]1=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 97411,3-DifluorobenzeneHCID 6451240Aluminum(III) ChlorideHCID 86751397HCID 86751397, compound

Product 1

HCID 10527851HCID 10527851, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2R)-2-[3-[4-(2,2,3,3-Tetrafluoropropoxy)phenyl]-2,3-dihydro-2-oxo-1H-imidazol-1-yl]propanoyl chloride (1.5 g) was dissolved in 30 ml of dichloromethane, to which 3.8 ml of 1,3-difluorobenzene and 2.3 g of anhydrous aluminum chloride (powder) were added. The mixture was refluxed with heating for 5 hours. The reaction solution was cooled, poured into 100 ml of ice water and extracted with 100 ml of ethyl acetate. The extract was washed with 50 ml of 1N-hydrochloric acid and 50 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: 50 g, eluent; hexane:ethyl acetate:acetic acid=2:1:0.03) and crystallized from 10 ml of diisopropyl ether to give 0.25 g of 1-[(1R)-2-(2,4-difluorophenyl)-2-oxo-1-methylethyl]-3-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2(1H,3H)-imidazolone as colorless powdery crystals.

Workup

  1. additionwere added
  2. temperatureThe mixture was refluxed
  3. temperaturewith heating for 5 hours
  4. temperatureThe reaction solution was cooled
  5. extractionextracted with 100 ml of ethyl acetate
  6. washThe extract was washed with 50 ml of 1N-hydrochloric acid and 50 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: 50 g, eluent; hexane:ethyl acetate:acetic acid=2:1:0.03)
  10. customcrystallized from 10 ml of diisopropyl ether

Sources & evidence

ORD record
ord-970c40c6387746b8a3ad9bdf20678bf5
Source dataset
uspto-grants-1997_10
Patent number
US05677464

Reaction notes

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