Potassium Carbonate → 3-BroMo-9-dibenzothiophen-4-yl-9H-carbazole

HRID 1753711Notes

Reaction equation

I[C:2]1[C:7]2[S:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br:15][C:16]1[CH:17]=[CH:18][C:19]2[NH:20][C:21]3[C:26]([C:27]=2[CH:28]=1)=[CH:25][CH:24]=[CH:23][CH:22]=3.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[Br:15][C:16]1[CH:17]=[CH:18][C:19]2[N:20]([C:2]3[C:7]4[S:8][C:9]5[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=5[C:6]=4[CH:5]=[CH:4][CH:3]=3)[C:21]3[C:26]([C:27]=2[CH:28]=1)=[CH:25][CH:24]=[CH:23][CH:22]=3

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 10.9 g (35.1 mmol) 4-iododibenzo[b,d]thiophene, 8.6 g (35.1 mmol) of 3-bromo-9H-carbazole, 4.46 g (70.2 mmol) of Cu, 14.55 g (100.1 mmole) of K2CO3 was stirred in 100 ml dimethylformamide, the reaction mixture was then heat to 160° C. for about overnight under nitrogen. Then cooled to 100° C., the solution was filtered. To receive the filtrate, and most of the dimethylformamide was removed under reduced pressure from the filtrate. The distillation was extracted with ethyl acetate and water, dried with anhydrous magnesium sulfate, the solvent was removed and the residue was purified by column chromatography on silica(hexane-dichloromethane) to give product 8.7 g (58%).

Workup

temperatureThen cooled to 100° C.
filtrationthe solution was filtered
custommost of the dimethylformamide was removed under reduced pressure from the filtrate
distillationThe distillation
extractionwas extracted with ethyl acetate and water
dry with materialdried with anhydrous magnesium sulfate
customthe solvent was removed
customthe residue was purified by column chromatography on silica(hexane-dichloromethane)

Sources & evidence

ORD record: ord-ed4349a937544c788dc954b69968377a
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09166177B2

Reaction notes

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