Hydrochloric Acid → 2-(5-Bromo-2-cyclopropylphenyl)cyclopentane-1,3-dione

HRID 339476

Reaction equation

HRID 339476 reaction equation
[C:1]1(=[O:7])[CH2:5][CH2:4][C:3](=[O:6])[CH2:2]1.C1(C)C=CC=CC=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Br:27][C:28]1[CH:29]=[CH:30][C:31]([CH:35]2[CH2:37][CH2:36]2)=[C:32]([Pb+3])[CH:33]=1.Cl>C(Cl)(Cl)Cl.ClCCl>[Br:27][C:28]1[CH:33]=[CH:32][C:31]([CH:35]2[CH2:37][CH2:36]2)=[C:30]([CH:2]2[C:3](=[O:6])[CH2:4][CH2:5][C:1]2=[O:7])[CH:29]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 774661,3-CyclopentanedioneHCID 178419342HCID 178419342, compound

Product 1

HCID 666768602-(5-Bromo-2-cyclopropylphenyl)cyclopentane-1,3-dione

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of cyclopentane-1,3-dione (0.57 g, 0.0058 mol) and N,N-dimethylaminopyridine (3.64 g, 0.030 mol) in chloroform (33 ml) is added toluene (9 ml) then 5-bromo-2-cyclopropylphenyl lead triacetate (3.77 g, 0.0065 mol). This solution is heated at 80° C. for 20 hours then cooled to room temperature and dilluted with dichloromethane and 2M aqueous hydrochloric acid. The resulting biphasic suspension is filtered through diatomaceous earth and the two phases are separated. The organic layer is further washed with 2M aqueous hydrochloric acid and the aqueous phase is extracted again with dichloromethane. All organic fractions are combined, washed with brine, dried over magnesium sulfate then concentrated in vacuo. The crude product is finally purified by flash column chromatography on silica gel (isohexane/ethyl acetate eluant) to afford 2-(5-bromo-2-cyclopropylphenyl)cyclopentane-1,3-dione as a pale yellow solid.

Workup

  1. temperaturethen cooled to room temperature
  2. filtrationThe resulting biphasic suspension is filtered through diatomaceous earth
  3. customthe two phases are separated
  4. washThe organic layer is further washed with 2M aqueous hydrochloric acid
  5. extractionthe aqueous phase is extracted again with dichloromethane
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationthen concentrated in vacuo
  9. customThe crude product is finally purified by flash column chromatography on silica gel (isohexane/ethyl acetate eluant)

Sources & evidence

ORD record
ord-551c3ce23a114421a780d304ee390544
Source dataset
uspto-grants-2014_11
Patent number
US08895474B2

Linked notes

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