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Hydrochloric Acid → (4-(9-Phenyl-9H-carbazol-3-yl)phenyl)boronic acid

HRID 1751327
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HRID 1751327 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:13]4[C:18]([C:19]=3[CH:20]=2)=[CH:17][CH:16]=[CH:15][CH:14]=4)=[CH:4][CH:3]=1.CCCCCC.C([Li])CCC.[B:38]([O:43]C)(OC)[O:39]C.Cl>O1CCCC1>[C:21]1([N:12]2[C:11]3[CH:10]=[CH:9][C:8]([C:5]4[CH:4]=[CH:3][C:2]([B:38]([OH:43])[OH:39])=[CH:7][CH:6]=4)=[CH:20][C:19]=3[C:18]3[C:13]2=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 313Hydrochloric Acid2회HCID 8470Trimethyl borate2회HCID 513582933-(4-Bromophenyl)-9-phenylcarbazoleHCID 178418244HCID 178418244, 화합물2회

생성물 1

HCID 58351149(4-(9-Phenyl-9H-carbazol-3-yl)phenyl)boronic acid수율 88%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5648413b516d4ad1b7f91fd831f3a551
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09159942B2

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