Hydrochloric Acid → 3-(4'-Chloro-3-methylbiphen-4-yl)bicyclo[3.2.1]octane-2,4-dione

HRID 72298Notes

Reaction equation

HRID 72298 reaction equation
C(Cl)(Cl)Cl.[C:5]([O-:8])(=O)[CH3:6].[C:9]([O-:12])(=O)[CH3:10].C([O-])(=O)C.[Cl:17][C:18]1[CH:31]=[CH:30][C:21]([C:22]2[CH:27]=[C:26]([CH3:28])[C:25]([Pb+3])=[CH:24][CH:23]=2)=[CH:20][CH:19]=1.Cl.[C:33]1(C)[CH:38]=CC=[CH:35][CH:34]=1>CN(C)C1C=CN=CC=1>[Cl:17][C:18]1[CH:31]=[CH:30][C:21]([C:22]2[CH:27]=[C:26]([CH3:28])[C:25]([CH:6]3[C:5](=[O:8])[CH:34]4[CH2:35][CH:10]([CH2:38][CH2:33]4)[C:9]3=[O:12])=[CH:24][CH:23]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 6212ChloroformHCID 178476523HCID 178476523, compound

Product 1

HCID 1317318323-(4'-Chloro-3-methylbiphen-4-yl)bicyclo[3.2.1]octane-2,4-dione

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Conditions

Temperature
80 °C

Procedure

Bicyclo[3.2.1]-2,4-dione (0.20 g, 1.44 mmol) and 4-dimethylaminopyridine (0.88 g, 7.21_mmol) are added to a mixture of chloroform (4 ml) and toluene (1 ml), and the reaction mixture is flushed with nitrogen for 15 minutes at ambient temperature. 4′-Chloro-3-methylbiphen-4-yllead triacetate (0.95 g, 1.6 mmol) is added in one portion and the reaction mixture is stirred and heated to 80° C. under an atmosphere of nitrogen for 1 hour. The reaction mixture is cooled to room temperature, acidified to pH 1 with 2N aqueous hydrochloric acid, filtered through a plug of diatomaceous earth and the two phases separated. The aqueous phase is extracted with dichloromethane (2×5 ml), the organic phases are combined, washed with water, and dried over anhydrous sodium sulfate. The mixture is filtered, and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give 3-(4′-chloro-3-methylbiphen-4-yl)bicyclo[3.2.1]octane-2,4-dione.

Workup

  1. customthe reaction mixture is flushed with nitrogen for 15 minutes at ambient temperature
  2. temperatureThe reaction mixture is cooled to room temperature
  3. filtrationfiltered through a plug of diatomaceous earth
  4. customthe two phases separated
  5. extractionThe aqueous phase is extracted with dichloromethane (2×5 ml)
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationThe mixture is filtered
  9. customthe filtrate is evaporated under reduced pressure
  10. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-3b266302d40c46c7a3e0215aa4fdbee6
Source dataset
uspto-grants-2014_09
Patent number
US08828908B2

Reaction notes

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