Water → Triphenylene

HRID 1253380

Reaction equation

HRID 1253380 reaction equation
[C:1]1([C:7]2[C:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].O>CC(N(C)C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:12]1[C:7]2[C:1]3[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 962WaterHCID 6766O-TerphenylHCID 11430Potassium Carbonate

Product 1

HCID 9170TriphenyleneYield 35%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 31374DimethylacetamideSolvent

Procedure

2.87 mmol of the o-terphenyl derivative, 0.14 mmol of Pd(OAc)2 and 5.7 mmol of K2CO3 are heated in 7 ml of DMA at 135° C. for 24 hours under a nitrogen atmosphere. The reaction mixture is cooled, treated with 5 ml of water and extracted with dichloromethane. The organic phase is dried, the solvent is removed under reduced pressure and the residue is purified by means of a short silica gel column (dichloromethane). After column chromatography (dichloromethane/hexane, 2:1), the desired triphenylene derivative (IIa) is obtained in from 35 to 40% yield.

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionextracted with dichloromethane
  3. customThe organic phase is dried
  4. customthe solvent is removed under reduced pressure
  5. customthe residue is purified by means of a short silica gel column (dichloromethane)

Sources & evidence

ORD record
ord-bed0d9afd4144f1387089f43035b718c
Source dataset
uspto-grants-2013_06
Patent number
US08455112B2

Linked notes

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