Toluene → HCID 49787146, compound

HRID 1470884Notes

Reaction equation

HRID 1470884 reaction equation
[CH3:1][C:2]1([CH3:12])[C:7](=[O:8])[CH2:6][C:5](=[O:9])[C:4]([CH3:11])([CH3:10])[O:3]1.C1(C)C=CC=CC=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Br:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=2)=[CH:35][C:34]=1[Pb+3]>C(Cl)(Cl)Cl.Cl>[Br:32][C:33]1[CH:34]=[CH:35][C:36]([C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=2)=[CH:37][C:38]=1[CH:6]1[C:7](=[O:8])[C:2]([CH3:12])([CH3:1])[O:3][C:4]([CH3:11])([CH3:10])[C:5]1=[O:9]

Participants

6

Reactant 3

HCID 1140TolueneHCID 199092752,2,6,6-Tetramethyloxane-3,5-dioneHCID 178476544HCID 178476544, compound

Product 1

HCID 49787146HCID 49787146, compoundYield 0.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6212ChloroformSolvent2×

Procedure

To a mixture of 2,2,6,6-tetramethylpyran-3,5-dione (0.75 g, 4.9 mmol) and N,N-dimethylaminopyridine (2.52 g, 20.6 mmol) is added anhydrous chloroform (40 ml), followed by stirring at room temperature until dissolution. To this solution is added anhydrous toluene (12 ml), followed by 4-bromo-4′-chlorobiphenyl-3-yllead triacetate (3.25 g, 5.1 mmol) in one portion and the reaction mixture is heated at 80° C. for 2 hours. The mixture is cooled to room temperature, diluted with chloroform (50 ml) and 1M aqueous hydrochloric acid (50 ml), and the mixture is stirred for 5 minutes. The precipitate is removed by filtration, the two phases separated, and the organic phase is washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated in vacuo. The residue is purified by flash column chromatography on silica gel, and fractions containing the desired compound are combined and evaporated to give a residue which is further purified by preparative reverse phase HPLC to give 4-(4-bromo-4′-chlorobiphenyl-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione (0.013 g).

Workup

  1. temperaturethe reaction mixture is heated at 80° C. for 2 hours
  2. temperatureThe mixture is cooled to room temperature
  3. stirringthe mixture is stirred for 5 minutes
  4. customThe precipitate is removed by filtration
  5. customthe two phases separated
  6. washthe organic phase is washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe filtrate is evaporated in vacuo
  10. customThe residue is purified by flash column chromatography on silica gel, and fractions
  11. additioncontaining the desired compound
  12. customevaporated
  13. customto give a residue which
  14. customis further purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-fba86473b85b4a8bbc7b1d3177fb4b3b
Source dataset
uspto-grants-2015_04
Patent number
US09006429B2

Reaction notes

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