Potassium Carbonate → HCID 59537038, compound

HRID 1919792Notes

Reaction equation

HRID 1919792 reaction equation
Br[C:2]1[CH:10]=[CH:9][C:8](Br)=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:12])[CH2:6]2.[C:13]1(B(O)O)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[C:13]1([C:2]2[CH:10]=[CH:9][C:8]([C:21]3[C:22]4[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:18]=[CH:19][CH:20]=3)=[C:7]3[C:3]=2[CH:4]=[C:5]([CH3:12])[CH2:6]3)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 57723635HCID 57723635, compound

Product 1

HCID 59537038HCID 59537038, compoundYield 65.5%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

In a 500 ml roundbottom flask were placed 17.6 g (61.1 mmol) 4,7-Dibromo-2-methyl-1H-indene, 26.3 g (2.5 eq.) 1-napthyl boronic acid, 274 mg (2 mol %) palladium acetate, 42.23 g (2.5 eq.) potassium carbonate, 39.4 g (2 eq.) tetrabutylammonium bromide, 169 ml degassed water and 169 ml degassed toluene. The mixture was stirred under reflux for 20 h. After cooling to room temperature, 100 ml toluene and 100 ml water were added. The aqueous phase was extracted 3 times with 100 ml toluene. The combined organic layers were washed once with 100 ml of 2M sodium hydroxide solution and 3 times with 50 ml water each, and dried over magnesium sulfate. Removal of the solvent in vacuo and purification via flash chromatography on silica using heptane/dichloromethane (10:1) yielded 15.3 g (40 mmol, 65%) of the desired indene as a white solid. 1H-NMR (500 MHz, CDCl3): δ=8.11, 7.89-7.77, 7.57-7.26 (3×m, 16H, aromatic), 6.61, 6.18 (2×s, 1H, indenyl-C═CH), 3.49 (“d”, 2H, benzylic), 2.09 (2×s, 3H, CH3) ppm.

Workup

  1. customIn a 500 ml roundbottom flask were placed
  2. customdegassed toluene
  3. temperatureunder reflux for 20 h
  4. addition100 ml toluene and 100 ml water were added
  5. extractionThe aqueous phase was extracted 3 times with 100 ml toluene
  6. washThe combined organic layers were washed once with 100 ml of 2M sodium hydroxide solution and 3 times with 50 ml water each, and
  7. dry with materialdried over magnesium sulfate
  8. customRemoval of the solvent
  9. customin vacuo and purification via flash chromatography on silica

Sources & evidence

ORD record
ord-fcb8448ea3dc4dea823427e1b7c2436e
Source dataset
uspto-grants-2012_05
Patent number
US08168556B2

Reaction notes

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