Toluene → 4-(5-Bromo-2-ethylphenyl)-2,2,6,6-tetramethylthiopyran-3,5-dione

HRID 1191586Notes

Reaction equation

HRID 1191586 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])[S: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:34]=[CH:35][C:36]([CH2:40][CH3:41])=[C:37]([Pb+3])[CH:38]=1>C(Cl)(Cl)Cl.ClCCl.Cl>[Br:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:40][CH3:41])=[C:35]([CH:6]2[C:7](=[O:8])[C:2]([CH3:12])([CH3:1])[S:3][C:4]([CH3:11])([CH3:10])[C:5]2=[O:9])[CH:34]=1

Participants

7

Reactant 3

HCID 1140TolueneHCID 156501652,2,6,6-Tetramethylthiopyran-3,5-dioneHCID 178476533HCID 178476533, compound

Product 1

HCID 684876664-(5-Bromo-2-ethylphenyl)-2,2,6,6-tetramethylthiopyran-3,5-dione

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,2,6,6-tetramethylthiopyran-3,5-dione (prepared according to the procedure of E. Er and P. Margaretha, Helvetica Chimica Acta (1992), 75(7), 2265-69) (1.8 g, 9.9 mmol) and N,N-dimethylaminopyridine (5.3 g, 4.34 mmol) in chloroform (60 ml), is added toluene (18 ml) then 5-bromo-2-ethylphenyllead triacetate (6.2 g, 1.09 mmol) in one portion. The resulting mixture is heated at reflux for 2 hours, then allowed to cool to ambient temperature, diluted with dichloromethane and 1M aqueous hydrochloric acid, and the organic phase is separated. The organic phase is concentrated under reduced pressure, and the residue is purified by flash chromatography on silica gel (hexane/ethyl acetate 95:5 to 7:3 ratio), giving 4-(5-bromo-2-ethylphenyl)-2,2,6,6-tetramethylthiopyran-3,5-dione (2.42 g) as an orange solid.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux for 2 hours
  3. customthe organic phase is separated
  4. concentrationThe organic phase is concentrated under reduced pressure
  5. customthe residue is purified by flash chromatography on silica gel (hexane/ethyl acetate 95:5 to 7:3 ratio)

Sources & evidence

ORD record
ord-439a742c8c394363aa0340d0bff9149a
Source dataset
uspto-grants-2014_03
Patent number
US08680012B2

Reaction notes

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