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

HRID 1751327
ノート
印刷プレビュー

反応式

HRID 1751327 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 313Hydrochloric Acid2 回HCID 8470Trimethyl borate2 回HCID 513582933-(4-Bromophenyl)-9-phenylcarbazoleHCID 178418244HCID 178418244、化合物2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5648413b516d4ad1b7f91fd831f3a551
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09159942B2

反応ノート

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