反应详情

In a 300-mL three-neck flask was put 8.0 g (20 mmol) of the 3-(4-bromophenyl)-9-phenyl-9H-carbazole obtained in Reaction Scheme (b-1), the atmosphere in the flask was replaced with nitrogen, 100 mL of dehydrated tetrahydrofuran (abbreviation: THF) was then added to the flask, and the temperature was lowered to −78° C. Into this mixture solution, 15 mL (24 mmol) of a 1.65 mol/L n-butyllithium hexane solution was dropped, and the mixture solution with the n-butyllithium hexane solution added was stirred for 2 hours. To this mixture, 3.4 mL (30 mmol) of trimethyl borate was added, and the mixture with the trimethyl borate added was stirred at −78° C. for 2 hours and at room temperature for 18 hours. After the reaction, 1M diluted hydrochloric acid was added to this reaction solution until the solution became acid, and the solution with the diluted hydrochloric acid added was stirred for 7 hours. This solution was subjected to ethyl acetate extraction, and the obtained organic layer was washed with a saturated saline. After the washing, magnesium sulfate was added to the organic layer to adsorb moisture. This suspension was filtered, and the obtained filtrate was concentrated, and hexane was added thereto. The mixture was irradiated with supersonic waves and then recrystallized, so that 6.4 g of a target substance was obtained as a white powder in a yield of 88%. A reaction scheme of Step 2 is shown in (b-2) given below.

1. customIn a 300-mL three-neck flask was put
2. additionwas then added to the flask
3. customwas lowered to −78° C
4. stirringwas stirred at −78° C. for 2 hours and at room temperature for 18 hours
5. additionwas added to this reaction solution until the solution
6. stirringwas stirred for 7 hours
7. extractionThis solution was subjected to ethyl acetate extraction
8. washthe obtained organic layer was washed with a saturated saline
9. additionAfter the washing, magnesium sulfate was added to the organic layer
10. filtrationThis suspension was filtered
11. concentrationthe obtained filtrate was concentrated
12. additionhexane was added
13. customThe mixture was irradiated with supersonic waves
14. customrecrystallized, so that 6.4 g of a target substance
15. customwas obtained as a white powder in a yield of 88%
16. customA reaction scheme of Step 2