Potassium Phosphate, Tribasic → HCID 58502816, compound

HRID 40468Notes

Reaction equation

HRID 40468 reaction equation
Br[C:2]1[C:3](=[O:9])[CH2:4][CH2:5][C:6]=1[O:7][CH3:8].[Cl:10][C:11]1[CH:27]=[CH:26][C:14]([C:15]2[CH:16]=[CH:17][C:18]([CH2:24][CH3:25])=[C:19](B(O)O)[CH:20]=2)=[CH:13][CH:12]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[Cl:10][C:11]1[CH:27]=[CH:26][C:14]([C:15]2[CH:20]=[CH:19][C:18]([CH2:24][CH3:25])=[C:17]([C:2]3[C:3](=[O:9])[CH2:4][CH2:5][C:6]=3[O:7][CH3:8])[CH:16]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 110954262-Bromo-3-methoxycyclopent-2-enoneHCID 594459274'-Chloro-4-ethylbiphenyl-3-ylboronic acid

Product 1

HCID 58502816HCID 58502816, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylCatalyst

Conditions

Temperature
90 °C

Procedure

To a stirred suspension of 2-bromo-3-methoxycyclopent-2-enone (1.0 g, 5.23 mmol), 4′-chloro-4-ethylbiphen-3-ylboronic acid (2.03 g, 7.80 mmol) and potassium phosphate (2.23 g, 10.50 mmol) in anhydrous, degassed toluene (25 ml) under an atmosphere of nitrogen is added palladium(II)acetate (24 mg, 0.105 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (86 mg, 0.209 mmol). The reaction is heated at 90° C. for 4 hours and then allowed to cool to room temperature, quenched with water (40 ml) and extracted with ethyl acetate (3×30 ml). The organic extracts are combined, washed with brine (15 ml), dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The residue is purified by column chromatography on silica gel to give 2-(4′-chloro-4-ethylbiphen-3-yl)-3-methoxycyclopent-2-enone (1.29 g, 75%).

Workup

  1. customdegassed toluene (25 ml) under an atmosphere of nitrogen
  2. temperatureto cool to room temperature
  3. customquenched with water (40 ml)
  4. extractionextracted with ethyl acetate (3×30 ml)
  5. washwashed with brine (15 ml)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe filtrate is evaporated under reduced pressure
  9. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d3c54b276b0a4d53ae8e78a0751849de
Source dataset
uspto-grants-2013_09
Patent number
US08530388B2

Reaction notes

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