4,4'-Difluorobenzophenone → HCID 15133033, compound

HRID 1086101Notes

Reaction equation

HRID 1086101 reaction equation
[Li].[F:2][C:3]1[CH:17]=[CH:16][C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=O)=[CH:5][CH:4]=1.[F:18][C:19]([F:24])([F:23])[C:20]([CH3:22])=O>O1CCCC1.CCCCCC.[Cl-].[Cl-].[Cl-].[Ti+3]>[F:18][C:19]([F:24])([F:23])[C:20]([CH3:22])=[C:7]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)[C:6]1[CH:16]=[CH:17][C:3]([F:2])=[CH:4][CH:5]=1

Participants

7

Reactant 3

HCID 95824,4'-DifluorobenzophenoneHCID 9871Methyl trifluoromethyl ketoneHCID 3028194Lithium

Product 1

HCID 15133033HCID 15133033, compoundYield 23.5%

Reagents, catalysts & solvents 3

HCID 10313229titanium(III) trichlorideCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

Lithium (1.94 g, 280 mmol) was added to a suspension of titanium trichloride (12.3 g, 80 mmol) in 250 mL tetrahydrofuran. After the initial exothermic reaction had subsided, the mixture was heated at reflux for 2 hours. After cooling to 25° C. a solution of 4,4'-difluorobenzophenone (2.18 g, 10 mmol) and 1,1,1-trifluoroacetone (4.48 g, 40 mmol) in 30 mL tetrahydrofuran was added and the mixture stirred for 2 hours. The mixture was then refluxed for 20 hours. The mixture was cooled and diluted with 30 mL of hexane and the insolubles removed by filtration through diatomaceous earth. The solution was concentrated in vacuo and the residue purified by chromatography on silica eluting with hexane to give 0.7 g of the title compound as an oil. MS(CI): m/e =298 for M+ of C16H11F5.

Workup

  1. customAfter the initial exothermic reaction
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 2 hours
  4. additionwas added
  5. temperatureThe mixture was then refluxed for 20 hours
  6. temperatureThe mixture was cooled
  7. customthe insolubles removed by filtration through diatomaceous earth
  8. concentrationThe solution was concentrated in vacuo
  9. customthe residue purified by chromatography on silica eluting with hexane

Sources & evidence

ORD record
ord-80bff69a190c4950bad64c7f3b204f8a
Source dataset
uspto-grants-1991_04
Patent number
US05011947

Reaction notes

Loading…