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Hydrochloric Acid → 4-(10-Phenylanthracen-9-yl)benzeneboronic acid

HRID 546651
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HRID 546651 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[C:14]([C:15]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[C:16]4[C:21]=2[CH:20]=[CH:19][CH:18]=[CH:17]4)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:4][CH:3]=1.C([Li])CCC.[B:33]([O:38]C)(OC)[O:34]C.Cl>O1CCCC1>[C:5]1([C:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:15]([C:22]3[CH:23]=[CH:24][C:25]([B:33]([OH:38])[OH:34])=[CH:26][CH:27]=3)=[C:16]3[C:21]=2[CH:20]=[CH:19][CH:18]=[CH:17]3)[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1
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참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8470Trimethyl borateHCID 221382759-(4-Bromophenyl)-10-phenylanthraceneHCID 178418339Butyllithium

생성물 1

HCID 235741214-(10-Phenylanthracen-9-yl)benzeneboronic acid수율 84%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran
용매

반응 조건

온도
-78 °C

실험 절차

20.0 g (48.9 mmol) of 9-(4-bromophenyl)-10-phenylanthracene was put into a 500 mL three-necked flask. Then, the atmosphere in the flask was substituted with nitrogen. After 300 mL of tetrahydrofuran (abbreviation: THF) was added to this flask, the flask was put into a constant low temperature bath and the reaction solution was cooled to −78° C. 34.2 mL (53.8 mmol) of n-butyllithium (1.57 mol/L hexane solution) was dropped into this solution and the solution was stirred at −78° C. for 2 hours. Thereafter, 12.6 mL (112 mmol) of trimethyl borate was added to the solution. Then, the flask was taken out from the constant low temperature bath, and the reaction solution was stirred for 24 hours to be returned to room temperature. After the reaction was completed, 200 mL of 1.0 mol/L hydrochloric acid was added to the reaction solution and the reaction solution was stirred at room temperature for 1 hour. An organic layer of the mixture was washed with water and the aqueous layer was extracted with ethyl acetate. The extracted solution was mixed with the organic layer, and the mixture was washed with a saturated aqueous sodium chloride solution, and then dried over magnesium sulfate. After the drying, this mixture was subjected to suction filtration, and the filtrate was condensed to obtain a residue. The obtained residue was recrystallized by a mixed solvent of chloroform and hexane; 15.3 g of objective 4-(10-phenyl-9-anthryl)phenylboronic acid was obtained as a white powdered solid in a yield of 84%. A synthetic scheme of 4-(10-phenyl-9-anthryl)phenylboronic acid is illustrated below (synthetic scheme b-5).

후처리

  1. customthe flask was put into a constant low temperature bath
  2. stirringthe reaction solution was stirred for 24 hours
  3. customto be returned to room temperature
  4. stirringthe reaction solution was stirred at room temperature for 1 hour
  5. washAn organic layer of the mixture was washed with water
  6. extractionthe aqueous layer was extracted with ethyl acetate
  7. additionThe extracted solution was mixed with the organic layer
  8. washthe mixture was washed with a saturated aqueous sodium chloride solution
  9. dry with materialdried over magnesium sulfate
  10. filtrationAfter the drying, this mixture was subjected to suction filtration
  11. customcondensed
  12. customto obtain a residue
  13. customThe obtained residue was recrystallized by a mixed solvent of chloroform and hexane

출처 및 근거

ORD 기록
ord-9df42ce3519645b6b53890adaa30f742
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07935854B2

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