Dimethylformamide → 7-bromo-12,12-dimethyl-10-(9,9-dimethyl-9H-fluorene-2-yl)-10,12-dihydroindeno[2,1-b]carbazole
Reaction equation
[CH3:1][C:2]1([CH3:37])[C:14]2[C:6]([N:7]=[C:8]3[C:13]=2[CH:12]=[CH:11][CH:10]=[CH:9]3)=[CH:5][C:4]2[CH:15]=[C:16]3[C:21]([C:3]1=2)=[CH:20][CH:19]([C:22]1[CH:34]=[CH:33][C:32]2[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:25]([CH3:36])([CH3:35])[C:24]=2[CH:23]=1)[CH:18]=[CH:17]3.CN(C=O)C.[Br:43]N1C(=O)CCC1=O>O>[Br:43][C:15]1[C:4]2[CH:5]=[C:6]3[C:14]([C:2]([CH3:37])([CH3:1])[C:3]=2[C:21]2[C:16]=1[CH:17]=[CH:18][CH:19]([C:22]1[CH:34]=[CH:33][C:32]4[C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[C:25]([CH3:36])([CH3:35])[C:24]=4[CH:23]=1)[CH:20]=2)=[C:13]1[C:8]([CH:9]=[CH:10][CH:11]=[CH:12]1)=[N:7]3Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
The resulting 12,12-dimethyl-10-(9,9-dimethyl-9H-fluorene-2-yl)-10,12-dihydroindeno[2,1-b]carbazole (7.0 g) and DMF (140 ml) were added to a reaction vessel. The mixture was heated up to 100° C., dissolved, and cooled. N-bromo-succinimide (2.6 g) was added under ice-cooled conditions, and the mixture was stirred for 1 hour at a room temperature. Water (500 ml) was added, and the mixture was subjected to filtration to obtain a pale red powder of 7-bromo-12,12-dimethyl-10-(9,9-dimethyl-9H-fluorene-2-yl)-10,12-dihydroindeno[2,1-b]carbazole (5.7 g; yield 70.3%).
Workup
- dissolutiondissolved
- temperaturecooled
- temperaturecooled conditions
- filtrationthe mixture was subjected to filtration
Sources & evidence
- ORD record
- ord-f8b84c621d064409825937dba45a54cc
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09196837B2
Reaction notes
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