Carbazole → 9H-3,9'-Bicarbazole

HRID 2045742Notes

Reaction equation

[C:1]([N:4]1[C:16]2[CH:15]=[CH:14][C:13](Br)=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)(=O)[CH3:2].[CH:18]1[C:30]2[NH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]=2C=C[CH:19]=1>[Cu]=O>[CH:15]1[C:16]2[N:4]([C:1]3[CH:19]=[CH:18][C:30]4[NH:29][C:28]5[C:23]([C:22]=4[CH:2]=3)=[CH:24][CH:25]=[CH:26][CH:27]=5)[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:11]=2[CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 170 °C

Procedure

A mixture of 4.0 g of 9-Acetyl-3-bromocarbazole prepared as described above and 2.8 g of carbazole were stirred together in 30 ml N,N′-dimethylacetamide. To this was added 0.8 g of copper oxide and heated to 170° C. for 24 h. The reaction was quenched with water and the solid was filtered, washed with methanol, and dried under vacuum. The solid (5.0 g) was then taken up for further deprotection using 1.2 g KOH with THF (6 ml), methanol (12 ml) and water (12 ml) at reflux temperature. The reaction mixture was then extracted using ethylacetate; and the organic layer was dried over anhydrous sodium sulfate and evaporated to dryness under vacuum. Subsequent silica gel column chromatography using toluene:hexane (1:2) as eluent, yielded 3.8 g of 3-(9-carbazolyl)carbazole as a white powder.

Workup

customprepared
customThe reaction was quenched with water
filtrationthe solid was filtered
washwashed with methanol
customdried under vacuum
temperatureat reflux temperature
extractionThe reaction mixture was then extracted
dry with materialand the organic layer was dried over anhydrous sodium sulfate
customevaporated to dryness under vacuum

Sources & evidence

ORD record: ord-43ed756ca0c243138eb7089c045943fd
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592055B2

Reaction notes

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