Chloranil → HCID 58289108, compound

HRID 1895567Notes

Reaction equation

HRID 1895567 reaction equation
[CH2:1]([S:9][C@H:10]1[C:31]2[C:22](=[CH:23][C:24]3[C:29]([CH:30]=2)=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@H:21]([S:32][CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:20]2[CH:19]=[C:18]3[C:13]([CH:14]=[CH:15][CH:16]=[CH:17]3)=[CH:12][C:11]1=2)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.ClC1C(=O)C(Cl)=C(Cl)C(=O)C=1Cl.C(=O)([O-])[O-].[K+].[K+]>C1C=CC=CC=1>[CH2:1]([S:9][C:10]1[C:31]2[C:22](=[CH:23][C:24]3[C:29]([CH:30]=2)=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:21]([S:32][CH2:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[C:20]2[C:11]=1[CH:12]=[C:13]1[C:18](=[CH:19]2)[CH:17]=[CH:16][CH:15]=[CH:14]1)[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8371ChloranilHCID 11430Potassium CarbonateHCID 178420290HCID 178420290, compound

Product 1

HCID 58289108HCID 58289108, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of trans-6,13-Bis(phenethylthio)-6,13-dihydropentacene (0.97 g, 1.76 mmol), tetrachloro-1,4-benzoquinone (0.87 g, 3.52 mmol) and potassium carbonate (2.43 g, 17.6 mmol) in dry benzene (170 mL) was stirred at 60° C. for 48 h under an argon atmosphere in the dark. After cooling to RT, the reaction mixture was filtered and washed with CH2Cl2. After evaporation of the filtrate, the solid residue was triturated with n-hexanes, filtered, and washed with hexane. After evaporation of the filtrate, the solid residue was passed through short column of n-Al2O3 eluted with CH2Cl2 and the deep blue band was collected. The solvent was evaporated to give pure 6,13-bis(phenethylthio)pentacene as deep blue solids in 72% yield (0.70 g). 1H NMR (500 MHz, CDCl3): δ 9.63 (s, 4H), 8.00 (m, 4H), 7.40 (m, 4H), 7.19 (m, 6H), 7.06 (d, 4H, J=7.08 Hz), 3.32 (t, 4H, J=7.56 Hz), 2.86 (t, 4H, J=7.56 Hz). 13C NMR (125.68 MHz, CDCl3): δ 140.91, 140.20, 132.83, 132.19, 128.88, 128.67, 128.52, 127.01, 126.49, 126.07, 38.97, 36.46. LDI-MS m/z: 550 [M+], UV-vis λmax(nm): 618, 571, 530.

Workup

  1. temperatureAfter cooling to RT
  2. filtrationthe reaction mixture was filtered
  3. washwashed with CH2Cl2
  4. customAfter evaporation of the filtrate
  5. customthe solid residue was triturated with n-hexanes
  6. filtrationfiltered
  7. washwashed with hexane
  8. customAfter evaporation of the filtrate
  9. washeluted with CH2Cl2
  10. customthe deep blue band was collected
  11. customThe solvent was evaporated

Sources & evidence

ORD record
ord-690f303a902942c0979933462ebc1fa2
Source dataset
uspto-grants-2013_08
Patent number
US08513466B2

Reaction notes

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