3-bromo-9-phenyl-9H-carbazole synthesis
- Product Name:3-bromo-9-phenyl-9H-carbazole
- CAS Number:1153-85-1
- Molecular formula:C18H12BrN
- Molecular Weight:322.2
1592-95-6
591-50-4
1153-85-1
The general procedure for the synthesis of 3-bromo-N-phenylcarbazole using 3-bromocarbazole and iodobenzene as starting materials was as follows: in a dry reaction flask, 3-bromo-9H-carbazole, iodobenzene, 0.03 equiv. of tris(dibenzylideneacetone)di-palladium(0) (Pd2(dba)3), 0.06 equiv. of tributylphosphine, and toluene (0.1 M) were added in sequence. The reaction mixture was stirred at room temperature for about 12 hours. Upon completion of the reaction, the mixture was cooled to ambient temperature, extracted with dichloromethane and the organic phase was washed with distilled water. The organic phase was collected and dried over anhydrous magnesium sulfate (MgSO4) and subsequently concentrated under reduced pressure. The residue was purified by column chromatography to afford the target product 3-bromo-9-phenyl-9H-carbazole in 87.22% yield. The exact mass of the compound was measured as 321 by high resolution mass spectrometry (HRMS) analysis and the molecular formula was confirmed as C18H12BrN.
Yield:1153-85-1 71%
Reaction Conditions:
with dibenzo-18-crown-6;potassium acetate;copper in N,N-dimethyl-formamide at 120; for 4 h;
Steps:
1.6 (6) Preparation Example 6: Synthesis of intermediate 1-4
3-bromo-9H-carbazole (2.5 g, 0.010 mol) in bromobenzene (1.6 g, 0.010 mol), dibenzo-18-crown-6 (1.1 g, 0.0030 mol), copper (2) (1.2 g, 0.020 mol) , into a 100 mL DMF to potassium acetate (2.8 g, 0.020 mol) it was reacted with stirring for 4 hours at 120 degree . After the reaction cooled to H20: After layer separation the MC column purification (n-Hexane: MC) to give to 2.3 g (yield 71%).
References:
P & H Tech Corporation;Hyun, Seo-Yong;Jung, Sung-wook;Kim, Dong-won KR2016/56521, 2016, A Location in patent:Paragraph 0159-0161
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