4-(Trimethylsilyl)phenylboronic Acid (contains varying amounts of Anhydride) → 4-(4-Trimethylsilyl-phenyl)-indene

HRID 627807Notes

Reaction equation

HRID 627807 reaction equation
[CH3:1][Si:2]([CH3:13])([CH3:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].Br[C:23]1[CH:31]=[CH:30][CH:29]=[C:28]2[C:24]=1[CH:25]=[CH:26][CH2:27]2>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH3:1][Si:2]([CH3:13])([CH3:12])[C:3]1[CH:8]=[CH:7][C:6]([C:23]2[CH:31]=[CH:30][CH:29]=[C:28]3[C:24]=2[CH:25]=[CH:26][CH2:27]3)=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 17104-(Trimethylsilyl)phenylboronic Acid (contains varying amounts of Anhydride)HCID 62657Potassium Phosphate, TribasicHCID 156376244-Bromo-1H-indene

Product 1

HCID 867251604-(4-Trimethylsilyl-phenyl)-indeneYield 79.2%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent2×

Procedure

In a 500-ml flask, 10.0 g (51.5 mmol) of 4-trimethylsilylphenylboronic acid and 200 ml of dimethoethane were added to make a solution and thereafter, 27.3 g (128 mmol) of potassium phosphate, 100 ml of water, 8.37 g (43.0 mmol) of 4-bromoindene, 0.22 g (0.86 mmol) of triphenylphosphine, and 0.300 g (0.430 mmol) of PdCl2(PPh3)2 were added in sequence and stirred under reflux for 12 hours. After cooling to room temperature, 100 ml of water was added. The organic phase was separated and then, the aqueous phase was extracted twice with 100 ml of ethyl acetate. The obtained organic phases were mixed and washed with a saline solution, and the resulting organic phase was dried by adding sodium sulfate. Sodium sulfate was filtered, and the solvent was removed by distillation under reduced pressure. The residue was purified on a silica gel column to obtain 9.0 g (yield: 79%) of 4-(4-trimethylsilyl-phenyl)-indene as a yellow liquid.

Workup

  1. temperatureunder reflux for 12 hours
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted twice with 100 ml of ethyl acetate
  4. additionThe obtained organic phases were mixed
  5. washwashed with a saline solution
  6. customthe resulting organic phase was dried
  7. additionby adding sodium sulfate
  8. filtrationSodium sulfate was filtered
  9. customthe solvent was removed by distillation under reduced pressure
  10. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-eb0e5a939ec0470caf77463e861fffde
Source dataset
uspto-grants-2016_04
Patent number
US09309340B2

Reaction notes

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