Hydrochloric Acid → HCID 49765293, compound

HRID 537670Notes

Reaction equation

HRID 537670 reaction equation
C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Br:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:21][CH3:22])=[C:18]([Pb+3])[CH:19]=1.[C:23]1(=[O:30])[CH2:28][CH2:27][CH2:26][C:25](=[O:29])[CH2:24]1.C1(C)C=CC=CC=1.Cl>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:21][CH3:22])=[C:18]([CH:24]2[C:25](=[O:29])[CH2:26][CH2:27][CH2:28][C:23]2=[O:30])[CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 104341,3-CyclohexanedioneHCID 178476533HCID 178476533, compound

Product 1

HCID 49765293HCID 49765293, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-bromo-2-ethylphenyllead triacetate (20.00 g, 35.2 mmol) (described in WO08/071,405) in chloroform (100 ml) is added cyclohexane-1,3-dione (3.94 g, 35.2 mmol) and 4-dimethylaminopyridine (22.36 g, 176 mmol). After stirring the reaction at room temperature for 5 minutes toluene (50 ml) is added and the solution is heated at 80° C. for 4 hours. After cooling to room temperature the mixture is allowed to stand overnight, followed by treatment with 2M aqueous hydrochloric acid. Following filtration of the precipitate the biphasic solution is separated, and the aqueous phase is extracted again with dichloromethane (×2). Organic fractions are combined then evaporated under reduced pressure to yield a crude product which is purified by flash column chromatography (10% ethyl acetate/hexane to 70% ethyl acetate/hexane eluant) to afford 2-(5-bromo-2-ethylphenyl)cyclohexane-1,3-dione as a white solid.

Workup

  1. additionis added
  2. temperatureAfter cooling to room temperature the mixture
  3. filtrationfiltration of the precipitate the biphasic solution
  4. customis separated
  5. extractionthe aqueous phase is extracted again with dichloromethane (×2)
  6. customOrganic fractions are combined then evaporated under reduced pressure
  7. customto yield a crude product which
  8. customis purified by flash column chromatography (10% ethyl acetate/hexane to 70% ethyl acetate/hexane eluant)

Sources & evidence

ORD record
ord-7d68571fb2e24128991a89d0db4d2ca2
Source dataset
uspto-grants-2014_10
Patent number
US08865623B2

Reaction notes

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