Sodium Carbonate → 5'-Chloro-1,1':3',1''-terphenyl

HRID 1907171Notes

Reaction equation

HRID 1907171 reaction equation
Br[C:2]1[CH:3]=[C:4]([Cl:9])[CH:5]=[C:6](Br)[CH:7]=1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O1CCCC1>[C:10]1([C:2]2[CH:3]=[C:4]([Cl:9])[CH:5]=[C:6]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:7]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic Acid2×HCID 846761,3-Dibromo-5-chlorobenzene

Product 1

HCID 44213325'-Chloro-1,1':3',1''-terphenylYield 163.3%

Reagents, catalysts & solvents 1

HCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

Into a 1 L four-necked glass flask equipped with a thermometer, a reflux condenser and a stirrer, 3,5-dibromochlorobenzene 20.0 g (74.0 mmol), phenylboronic acid 27.0 g (222 mmol), 2.0 mol/l sodium carbonate aqueous solution 285 ml (570 mmol), and toluene:tetrahydrofuran (1:1) solution 500 ml were added, and nitrogen was passed through the solution for 2 hours and 30 minutes. Tetrakistriphenylphosphine palladium(0) 4.28 g (3.70 mmol) was then added, which was reacted for 28 hours at 73 to 75° C. with stirring followed by further addition of phenylboronic acid 4.10 g (33.6 mmol) and tetrakistriphenylphosphine palladium(0) 1.10 g (950 μmol) and reaction for 24 hours at 73 to 75° C. with stirring. After completion of the reaction, the reaction mixture was cooled down to room temperature and separated with the addition of water and toluene, and after the water layer was extracted with toluene and after the organic layers were combined and washed with water, it was dried with anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the obtained concentrate was purified by silica-gel column chromatography (eluent: hexane) to obtain 3,5-diphenylchlorobenzene 16.0 g as white solid (isolation yield; 82%).

Workup

  1. additionwere added
  2. customwhich was reacted for 28 hours at 73 to 75° C.
  3. stirringwith stirring
  4. customAfter completion of the reaction
  5. customseparated with the addition of water and toluene
  6. extractionafter the water layer was extracted with toluene
  7. washwashed with water, it
  8. dry with materialwas dried with anhydrous magnesium sulfate
  9. filtrationAfter filtration
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. concentrationthe obtained concentrate
  12. customwas purified by silica-gel column chromatography (eluent: hexane)

Sources & evidence

ORD record
ord-f8af0d26154a4109825ff6c6e87fa024
Source dataset
uspto-grants-2013_12
Patent number
US08597799B2

Reaction notes

Loading…