Cesium carbonate → HCID 86657857, compound

HRID 1257560Notes

Reaction equation

HRID 1257560 reaction equation
[C:1]1(B(O)O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:21]1[C:29]([CH3:30])=[CH:28][CH:27]=[C:26]2[C:22]=1[CH:23]=[CH:24][CH2:25]2>C(COC)OC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]1([C:21]2[C:29]([CH3:30])=[CH:28][CH:27]=[C:26]3[C:22]=2[CH:23]=[CH:24][CH2:25]3)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2545321-Naphthaleneboronic acidHCID 58444066HCID 58444066, compound

Product 1

HCID 86657857HCID 86657857, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

1-Naphthylboronic acid (10 g, 58.1 mmol) was dissolved in dimethoxyethane (150 mL), and aqueous solution (100 mL) of cesium carbonate (25.3 g, 78 mmol), 4-bromo-5-methylindene (8.1 g, 39 mmol), tetrakis(triphenylphosphine)palladium (1.8 g) were sequentially added. Solution was reacted for 21 hours while heating under reflux, then, reaction solution was poured into 1N hydrochloric acid-ice water, and after stirring, reaction solution was extracted with diethyl ether. Organic layer was washed with magnesium sulfate, then, solvent was distilled off under reduced pressure to obtain the crude product. This was purified by silica-gel column chromatography to obtain the desired 4-(1-naphthyl)-5-methylindene (8.6 g, yield: 87%).

Workup

  1. customSolution was reacted for 21 hours
  2. temperaturewhile heating
  3. temperatureunder reflux
  4. customreaction solution
  5. customreaction solution
  6. extractionwas extracted with diethyl ether
  7. washOrganic layer was washed with magnesium sulfate
  8. distillationsolvent was distilled off under reduced pressure
  9. customto obtain the crude product
  10. customThis was purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-1d3b447ec8ed4b7d8e55538fb76c83eb
Source dataset
uspto-grants-2013_06
Patent number
US08461365B2

Reaction notes

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