ChemicalBook CAS DataBase List 3,6-Bis(trifluoromethyl)-9H-carbazole

3,6-Bis(trifluoromethyl)-9H-carbazole synthesis

6synthesis methods

Product Name:3,6-Bis(trifluoromethyl)-9H-carbazole
CAS Number:1355001-50-1
Molecular formula:C14H7F6N
Molecular Weight:303.2

7639-71-6 Synthesis

4-(trifluoromethyl)-N-[4-(trifluoromethyl)phenyl]aniline

7639-71-6
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1355001-50-1
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Yield:1355001-50-1 56%

Reaction Conditions:

with oxygen;palladium diacetate;acetic acid at 90; for 12 h;

Steps:

Synthesis of 3,6-bis(trfluoromethyl)-9H-carbazole int B3:

Step 3: To bis(4-(trifluoromethyl)phenyl)amine (5.4 g, 17.6mmol),was added acetic acid (54 mL) and Pd(OAc)₂(0.397 g, 1.76 mmol) and heated to 90 °C for 12 h under an oxygen balloon. Solid NaHCO₃ was added to quench the reaction and the mixture was diluted with ethyl acetate. The organic layer was dried with MgSO₄ and concentrated to give crude product. It was further purified by silica gel chromatography using 25% ethyl acetate/petroleum ether to afford 2.8 g of white solid (Yield: 56%). LCMS: (Method B) 303 (M+H), RT. 2.83 min, 99.88 % (max) ¹H NMR (400 MHz, CDCl₃): δ 12.12 (s, 1H), 8.81 (s, 2H), 7.75-7.77 (m, 2H), 7.73 (d, J = 8.00 Hz, 2H).

References:

WO2014/108168,2014,A1 Location in patent:Page/Page column 85; 86