Sodium Carbonate → HCID 11333990, compound

HRID 2269296Notes

Reaction equation

HRID 2269296 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[Cl:12][C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C(O)C>[Cl:12][C:13]1[CH:18]=[C:17]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[C:7](=[O:11])[CH2:6][CH2:5]3)[CH:16]=[CH:15][CH:14]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 5206955-Bromo-1-indanoneHCID 2734323(3-Chlorophenyl)boronic acid

Product 1

HCID 11333990HCID 11333990, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

3 g (14.2 mmol) of 5-bromoindan-1-one are suspended with 2.22 g (14.2 mmol) of 3-chlorophenylboronic acid and 3 g (28.3 mmol) of sodium carbonate in a mixture of 100 ml of toluene, 20 ml of ethanol and 20 ml of water. Under an argon atmosphere, 160 mg (7.1 mmol) of palladium(II) acetate and 373 mg (14.2 mmol) of triphenylphosphine are added. The mixture is heated under reflux for 3 h, and then the ethanol content of the solvent mixture is removed in vacuo. 40 ml of 0.5 N sodium hydroxide solution are added, and the mixture is stirred at room temperature for 10 min. The precipitate is filtered off with suction; the filtrate is washed with 40 ml of water until neutral and then washed with concentrated brine (3×40 ml), dried over magnesium sulfate, concentrated in vacuo and purified by chromatography on silica gel with toluene/ethyl acetate 20/1. 5-(3-Chlorophenyl)indan-1-one is obtained with a melting point of 113° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 3 h
  3. customthe ethanol content of the solvent mixture is removed in vacuo
  4. addition40 ml of 0.5 N sodium hydroxide solution are added
  5. filtrationThe precipitate is filtered off with suction
  6. washthe filtrate is washed with 40 ml of water until neutral and
  7. washthen washed with concentrated brine (3×40 ml)
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. custompurified by chromatography on silica gel with toluene/ethyl acetate 20/1

Sources & evidence

ORD record
ord-0c78e8a284a54a26825541f9c4a6c1cf
Source dataset
uspto-grants-2001_12
Patent number
US06329407B1

Reaction notes

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