Toluene → 2mDBTPDBq-II

HRID 882564Notes

Reaction equation

HRID 882564 reaction equation
Cl[C:2]1[CH:11]=[N:10][C:9]2[C:4](=[C:5]3[CH:19]=[CH:18][CH:17]=[CH:16][C:6]3=[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]3=2)[N:3]=1.[CH:20]1[C:28]2[C:27]3[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=3[S:25][C:24]=2[C:23]([C:33]2[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=2)=[CH:22][CH:21]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>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(O)C>[CH:20]1[C:28]2[C:27]3[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=3[S:25][C:24]=2[C:23]([C:33]2[CH:34]=[C:35]([C:2]3[CH:11]=[N:10][C:9]4[C:4](=[C:5]5[CH:19]=[CH:18][CH:17]=[CH:16][C:6]5=[C:7]5[CH:15]=[CH:14][CH:13]=[CH:12][C:8]5=4)[N:3]=3)[CH:36]=[CH:37][CH:38]=2)=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 580194962-Chlorodibenzo[f,h]quinoxalineHCID 58261920(3-(Dibenzo[b,d]thiophen-4-yl)phenyl)boronic acid

Product 1

HCID 584100172mDBTPDBq-II

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

First, 5.3 g (20 mmol) of 2-chlorodibenzo[f,h]quinoxaline, 6.1 g (20 mmol) of 3-(dibenzothiophen-4-yl)phenylboronic acid, 460 mg (0.4 mmol) of tetrakis(triphenylphosphine)palladium(0), 300 mL of toluene, 20 mL of ethanol, and 20 mL of a 2M aqueous solution of potassium carbonate were put in a 2-L three-neck flask. The mixture was degassed by being stirred under reduced pressure, and the air in the three-neck flask was replaced with nitrogen. This mixture was stirred under a nitrogen stream at 100° C. for 7.5 hours. After cooled to room temperature, the obtained mixture was filtered to give a white residue. The obtained residue was washed with water and ethanol in this order, and then dried. The obtained solid was dissolved in about 600 mL of hot toluene, followed by suction filtration through Celite and Florisil, whereby a clear colorless filtrate was obtained. The obtained filtrate was concentrated and purified by silica gel column chromatography using about 700 mL of silica gel. The chromatography was carried out using hot toluene as a developing solvent. Acetone and ethanol were added to the solid obtained here, followed by irradiation with ultrasonic waves. Then, the generated suspended solid was collected by filtration and the obtained solid was dried, so that 7.85 g of white powder was obtained in 80% yield.

Workup

  1. customThe mixture was degassed
  2. stirringThis mixture was stirred under a nitrogen stream at 100° C. for 7.5 hours
  3. filtrationthe obtained mixture was filtered
  4. customto give a white residue
  5. washThe obtained residue was washed with water and ethanol in this order
  6. customdried
  7. dissolutionThe obtained solid was dissolved in about 600 mL of hot toluene
  8. filtrationfollowed by suction filtration through Celite and Florisil, whereby a clear colorless filtrate
  9. customwas obtained
  10. concentrationThe obtained filtrate was concentrated
  11. custompurified by silica gel column chromatography
  12. additionAcetone and ethanol were added to the solid
  13. customobtained here
  14. customfollowed by irradiation with ultrasonic waves
  15. filtrationwas collected by filtration
  16. dry with materialthe obtained solid was dried, so that 7.85 g of white powder
  17. customwas obtained in 80% yield

Sources & evidence

ORD record
ord-490525716d6e4dec85a8c80bdd8d38ad
Source dataset
uspto-grants-2015_03
Patent number
US08994263B2

Reaction notes

Loading…