Potassium Phosphate, Tribasic → HCID 91247527, compound

HRID 72299Notes

Reaction equation

HRID 72299 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[CH2:8][CH3:9].[CH3:17][C:18]1([CH3:27])[CH:23]2[CH2:24][CH:19]1[C:20](=[O:26])[CH2:21][C:22]2=[O:25].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([C:4]2[CH:5]=[CH:6][C:7]([CH2:8][CH3:9])=[C:2]([CH:21]3[C:20](=[O:26])[CH:19]4[CH2:24][CH:23]([C:18]4([CH3:17])[CH3:27])[C:22]3=[O:25])[CH:3]=2)=[CH:11][CH:12]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 585864606,6-Dimethylbicyclo[3.1.1]heptane-2,4-dioneHCID 594459053-Bromo-4'-chloro-4-ethylbiphenyl

Product 1

HCID 91247527HCID 91247527, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
160 °C

Procedure

3-Bromo-4′-chloro-4-ethylbiphenyl (0.200 g, 0.68 mmol) is added to a mixture of 6,6-dimethylbicyclo[3.1.1]heptane-2,4-dione (0.124 g, 0.81 mmol), prepared by the method of W. Childers et al., US2006/0004108, powdered potassium phosphate (0.316 g, 1.49 mmol), palladium (II) acetate (0.008 g, 0.034 mmol) and (2-dicyclohexylphosphino)-2′,4′,6′-triisopropylbiphenyl (0.024 g, 0.051 mmol) in degassed 1,2-dimethoxyethane (2 ml) and the mixture is stirred and heated to 160° C. for 1 hour under microwave irradiation. The mixture is cooled to room temperature, diluted with ethyl acetate and washed with 2 M aqueous hydrochloric acid. The organic phase is washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The residue is taken up in N,N-dimethylformamide (2 ml) and purified by preparative reverse-phase HPLC to give 3-(4′-chloro-4-ethylbiphen-3-yl)-6,6-dimethylbicyclo[3.1.1]heptane-2,4-dione.

Workup

  1. customprepared by the method of W
  2. temperatureThe mixture is cooled to room temperature
  3. washwashed with 2 M aqueous hydrochloric acid
  4. washThe organic phase is washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate is evaporated under reduced pressure
  8. custompurified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-85af9ccff6274bd69bf48f352a97d2ec
Source dataset
uspto-grants-2014_09
Patent number
US08828908B2

Reaction notes

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