Chloranil → HCID 58289111, compound

HRID 1895572Notes

Reaction equation

HRID 1895572 reaction equation
[Cl:1][C:2]1[C:23]([Cl:24])=[CH:22][C:21]2[C:4](=[CH:5][C:6]3[C@@H:7]([S:36][CH2:37][CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[C:8]4[C:17]([C@H:18]([S:25][CH2:26][CH2:27][C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[C:19]=3[CH:20]=2)=[CH:16][C:15]2[C:10](=[CH:11][C:12]([Cl:35])=[C:13]([Cl:34])[CH:14]=2)[CH:9]=4)[CH:3]=1.ClC1C(=O)C(Cl)=C(Cl)C(=O)C=1Cl.C(=O)([O-])[O-].[K+].[K+]>C1C=CC=CC=1>[Cl:24][C:23]1[C:2]([Cl:1])=[CH:3][C:4]2[C:21](=[CH:20][C:19]3[C:6]([CH:5]=2)=[C:7]([S:36][CH2:37][CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:8]2[C:17](=[CH:16][C:15]4[C:10]([CH:9]=2)=[CH:11][C:12]([Cl:35])=[C:13]([Cl:34])[CH:14]=4)[C:18]=3[S:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:22]=1

Participants

5

Reactant 3

HCID 8371ChloranilHCID 11430Potassium CarbonateHCID 178477814HCID 178477814, compound

Product 1

HCID 58289111HCID 58289111, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2,3,9,10-tetrachloro-trans-6,13-bis(phenylethylthio)-6,13-dihydropentacene (0.3 g, 0.44 mmol), tetrachloro-1,4-benzoquinone (0.22 g, 0.89 mmol) and potassium carbonate (0.61 g, 4.45 mmol) in dry benzene (50 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 passed through short column of n-Al2O3 eluted with CH2Cl2 and the deep blue band was collected. The solvent was evaporated to give pure 2,3,9,10-tetrachloro-6,13-bis(phenethylthio)pentacene as deep blue solids in 17% yield (0.05 g). 1H NMR (500 MHz, CDCl3): δ 9.48 (s, 4H), 8.11 (s, 4H), 7.24 (m, 6H), 7.06 (m, 4H), 3.27 (t, 4H, J=7.32 Hz), 2.85 (t, 4H, J=7.32 Hz). 13C NMR (125.68 MHz, CDCl3): δ 132.89, 132.44, 132.25, 128.95, 128.73, 128.59, 127.07, 126.56, 126.14, 38.04, 36.53. LDI-MS m/z: 688 [M+], UV-vis λmax(nm): 628, 577, 537.

Workup

  1. temperatureAfter cooling to RT
  2. filtrationthe reaction mixture was filtered
  3. washwashed with CH2Cl2
  4. customAfter evaporation of the filtrate
  5. washeluted with CH2Cl2
  6. customthe deep blue band was collected
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-1d0c7131bcfe45b681c3bdb82ceb2952
Source dataset
uspto-grants-2013_08
Patent number
US08513466B2

Reaction notes

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