Methanol → HCID 58800340, compound

HRID 1913985Notes

Reaction equation

HRID 1913985 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:12]3=[CH:13][C:14]4[C:22](=[CH:23][C:11]3=[N:10][C:7]2=[CH:8][CH:9]=1)[C:21]1[C:16](=[CH:17][CH:18]=[C:19]([Cl:24])[CH:20]=1)[N:15]=4.Br[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].CO>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.CS(C)=O>[Cl:24][C:19]1[CH:20]=[C:21]2[C:22]3=[CH:23][C:11]4[N:10]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[C:7]5[C:6]([C:12]=4[CH:13]=[C:14]3[N:15]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:11][CH2:12][CH2:6][CH2:5][CH2:4][CH2:9][CH3:8])[C:16]2=[CH:17][CH:18]=1)=[CH:5][C:4]([Cl:3])=[CH:9][CH:8]=5

Participants

7

Reactant 4

HCID 887MethanolHCID 89191-BromododecaneHCID 14798Sodium HydroxideHCID 178477838HCID 178477838, compound

Product 1

HCID 58800340HCID 58800340, compoundYield 175.3%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

50% aqueous NaOH solution (4 mL) was added to a well-stirred mixture of 2,8-dichloroindolo[3,2-b]carbazole (0.65 g, 2 mmol) as prepared above, benzyltriethylammonium chloride (90 mg, 0.4 mmol), and 1-bromododecane (1.99 g, 8 mmol) in DMSO (20 mL) in a 100-mL flask, and the resultant mixture was stirred at room temperature for 1 h and then at 50° C. for 4 h. Subsequently, the mixture was poured into MeOH (200 mL), and the precipitated yellow solid was filtered and washed 3 times each with water, N,N-dimethylformamide, methanol, and acetone, yielding 1.16 g (88.0%) of 2,8-dichloro-5,11-didodecylindolo[3,2-b]carbazole, compound (3), after drying in vacuo. It was then subject to train sublimation to obtain electrically pure samples for OTFT fabrication.

Workup

  1. filtrationthe precipitated yellow solid was filtered
  2. washwashed 3 times each with water, N,N-dimethylformamide, methanol, and acetone

Sources & evidence

ORD record
ord-77ec4e8ac2b546c99d6c64e777a826d9
Source dataset
uspto-grants-2013_12
Patent number
US08609867B2

Reaction notes

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