Methanol → HCID 58800340, compound

HRID 273493Notes

Reaction equation

HRID 273493 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-c4a7897175d144159e7c2db1adc1d32c
Source dataset
uspto-grants-2008_11
Patent number
US07456424B2

Reaction notes

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