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

HRID 1967882
ノート
印刷プレビュー

反応式

HRID 1967882 の反応式
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
参加物反応条件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 AcidHCID 8470Trimethyl borateHCID 221382759-(4-Bromophenyl)-10-phenylanthraceneHCID 178418339Butyllithium

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran
溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2744eca02ce643cb843eafd102fa5257
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08420874B2

反応ノート

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