Chloranil → HCID 57913442, compound

HRID 1261743Notes

Reaction equation

HRID 1261743 reaction equation
[Br:1][C:2]1[CH:23]=[CH:22][C:21]2[S:20][C:19]3[C:6](=[CH:7][C:8]4[S:9][C:10]5[C:15]([CH:16]([C:24]6[CH:29]=[CH:28][C:27]([CH:30]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:26][CH:25]=6)[C:17]=4[CH:18]=3)=[CH:14][C:13]([Br:43])=[CH:12][CH:11]=5)[CH:5]([C:44]3[CH:49]=[CH:48][C:47]([CH:50]([CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62])[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])=[CH:46][CH:45]=3)[C:4]=2[CH:3]=1.C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>CO>[Br:43][C:13]1[CH:12]=[CH:11][C:10]2[S:9][C:8]3[C:17]([CH:18]=[C:19]4[C:6]([CH:7]=3)=[C:5]([C:44]3[CH:49]=[CH:48][C:47]([CH:50]([CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH3:62])=[CH:46][CH:45]=3)[C:4]3[C:21](=[CH:22][CH:23]=[C:2]([Br:1])[CH:3]=3)[S:20]4)=[C:16]([C:24]3[CH:25]=[CH:26][C:27]([CH:30]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:28][CH:29]=3)[C:15]=2[CH:14]=1

Participants

4

Reactant 2

HCID 8371ChloranilHCID 86635072HCID 86635072, compound

Product 1

HCID 57913442HCID 57913442, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 7.1 grams of 2,9-Dibromo-7,14-bis-[4-(1-hexyl-heptyl)-phenyl]-7,14-dihydro-5,12-dithia-pentacene and 2.6 grams of chloranil is heated in 100 ml ortho-dichloronezene at 150° C. for 4 hours. After cooling to 22° C., the reaction mixture is poured into 600 ml methanol, filtered off and washed three times with 50 ml methanol. The crude product is suspended in 80 ml acetone, stirred for one hour and filtered off. After drying in vacuum 3.0 grams 2,9-dibromo-7,14-bis-[4-(1-hexyl-heptyl)-phenyl]-5,12-dithia-pentacene are obtained as violet crystals. 1H-NMR(CHCl3): 7.26 (d, 4H, J=8 Hz); 7.04 (d, 4H, J=8 Hz); 6.98 (dd, 2H, J=8.5/2 Hz); 6.71 (d, 2H, J=8.5 Hz); 6.58 (d, 2H, J=2 Hz); 5.86 (s, 2H); 2.57 (m, 2H); 1.8-1.1 (m, 40H); 0.88 (t, 12H).

Workup

  1. temperatureAfter cooling to 22° C.
  2. filtrationfiltered off
  3. washwashed three times with 50 ml methanol
  4. filtrationfiltered off
  5. dry with materialAfter drying in vacuum 3.0 grams 2,9-dibromo-7,14-bis-[4-(1-hexyl-heptyl)-phenyl]-5,12-dithia-pentacene
  6. customare obtained as violet crystals

Sources & evidence

ORD record
ord-5ffacb35b1084c48b08d19181c53c458
Source dataset
uspto-grants-2013_06
Patent number
US08471019B2

Reaction notes

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