Water → 4-Phenyl-5-methylindene

HRID 1257556Notes

Reaction equation

HRID 1257556 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:17]1[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]2[C:18]=1[CH:19]=[CH:20][CH2:21]2.O>COCCOC.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:17]2[C:25]([CH3:26])=[CH:24][CH:23]=[C:22]3[C:18]=2[CH:19]=[CH:20][CH2:21]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 58444066HCID 58444066, compound

Product 1

HCID 231155034-Phenyl-5-methylindeneYield 86%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

phenylboronic acid (8.3 g, 68 mmol) was dissolved in ethylene glycol dimethylether (DME, 100 mL), and aqueous solution (100 mL) of cesium carbonate (30 g), 4-bromo-5-methylindene (10 g, 48 mmol), tetrakis(triphenylphosphine)palladium (3.0 g, 2.6 mmol) were sequentially added. Solution was reacted for 55 hours while heating under reflux, then, reaction solution was added into water (200 mL), and extracted with diisopropylether. Organic layer was washed with 1N hydrochloric acid and saturated aqueous solution of sodium chloride, then was dried over sodium sulfate, and solvent was distilled off under reduced pressure to obtain the crude product. This was purified by silica-gel column chromatography (Silica-gel 60: produced by Kanto Chemical Co., Inc, hexane) to obtain 4-phenyl-5-methylindene (8.5 g, yield: 86%) as colorless liquid.

Workup

  1. customSolution was reacted for 55 hours
  2. temperaturewhile heating
  3. temperatureunder reflux
  4. customreaction solution
  5. extractionextracted with diisopropylether
  6. washOrganic layer was washed with 1N hydrochloric acid and saturated aqueous solution of sodium chloride
  7. dry with materialwas dried over sodium sulfate, and solvent
  8. distillationwas distilled off under reduced pressure
  9. customto obtain the crude product
  10. customThis was purified by silica-gel column chromatography (Silica-gel 60: produced by Kanto Chemical Co., Inc, hexane)

Sources & evidence

ORD record
ord-839bbbff49434a55959b0998cef7ae6d
Source dataset
uspto-grants-2013_06
Patent number
US08461365B2

Reaction notes

Loading…