Sodium Carbonate → 2,8-Bis(2-thienyl)-5,11-didodecylindolo[3,2-b]carbazole

HRID 252670Notes

Reaction equation

HRID 252670 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1B(O)O.Br[C:10]1[CH:11]=[C:12]2[C:18]3=[CH:19][C:20]4[N:21]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[C:22]5[C:27]([C:28]=4[CH:29]=[C:17]3[N:16]([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[C:13]2=[CH:14][CH:15]=1)=[CH:26][C:25](Br)=[CH:24][CH:23]=5.C([O-])([O-])=O.[Na+].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].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.C1(C)C=CC=CC=1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:10]1[CH:11]=[C:12]2[C:18]3=[CH:19][C:20]4[N:21]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[C:22]5[C:27]([C:28]=4[CH:29]=[C:17]3[N:16]([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[C:13]2=[CH:14][CH:15]=1)=[CH:26][C:25]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)=[CH:24][CH:23]=5

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27339602-Thiopheneboronic acidHCID 58800344HCID 58800344, compound

Product 1

HCID 597495852,8-Bis(2-thienyl)-5,11-didodecylindolo[3,2-b]carbazole

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

ALIQUAT™ 336 (0.6 g), 2-thiopheneboronic acid (0.921 g, 7.2 mmol), 2,8-dibromo-5,11-didodecylindolo[3,2-b]carbazole (2.252 g, 3 mmol), 2M Na2CO3 solution (7.5 mL, 15 mmol), Pd(PPh3)4 (72 mg, 0.06 mmol) and toluene (10 mL) were added into a 50 mL flask. The mixture was heated to gentle reflux and maintained for 48 h. The reaction mixture was cooled down, organic layer separated, dried, and filtered. The toluene solution was passed through a silica gel column and the solvent was removed. Recrystallization from toluene gave the title compound as a yellow solid. Yield: 1.476 g (61%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto gentle reflux
  3. temperaturemaintained for 48 h
  4. temperatureThe reaction mixture was cooled down
  5. customorganic layer separated
  6. customdried
  7. filtrationfiltered
  8. customthe solvent was removed
  9. customRecrystallization from toluene

Sources & evidence

ORD record
ord-16f0701ba9224c2b823f771281273e96
Source dataset
uspto-grants-2011_01
Patent number
US07868186B2

Reaction notes

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