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

HRID 1910368
ノート
印刷プレビュー

反応式

HRID 1910368 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

実験手順

In a 500 mL three-neck flask were stirred 20 g (49 mmol) of 9-(4-Bromophenyl)-10-phenylanthracene obtained by the above Steps 1(1) to 1(4) and 300 mL of tetrahydrofuran (abbreviation: THF) in a nitrogen atmosphere at −78° C. Then, 34 mL (54 mmol) of n-butyllithium (1.6 mol/L hexane solution) was dropped, and this mixture was stirred for 2 hours at the same temperature. After that, 13 mL (110 mmol) of trimethyl borate was added therein, and the mixture was stirred for 24 hours at room temperature. After the reaction, 200 mL of 1.0 mol/L hydrochloric acid was added therein, and the mixture was stirred for 1 hour at room temperature. After that, an organic layer thereof was washed with water and separated into an organic layer and a water layer, and the obtained water layer was further extracted with ethyl acetate. This extracted solution and the organic layer were mixed and washed with saturated aqueous solution, and magnesium sulfate was added therein, so that moisture was removed. Then, suction filtration was performed so that a filtrate was obtained. The obtained filtrate was concentrated to provide a residue. The obtained residue was recrystallized with a mixed solution of chloroform and hexane, whereby 15 g of a powdery white solid of 4-(10-phenyl-9-anthryl)phenylboronic acid, which was the object of the synthesis, was obtained in a yield of 84% (synthesis scheme (a-5)).

後処理

  1. stirringthe mixture was stirred for 24 hours at room temperature
  2. additionwas added
  3. stirringthe mixture was stirred for 1 hour at room temperature
  4. washAfter that, an organic layer thereof was washed with water
  5. customseparated into an organic layer
  6. extractiona water layer, and the obtained water layer was further extracted with ethyl acetate
  7. additionThis extracted solution and the organic layer were mixed
  8. washwashed with saturated aqueous solution, and magnesium sulfate
  9. additionwas added
  10. customso that moisture was removed
  11. filtrationThen, suction filtration
  12. customwas obtained
  13. concentrationThe obtained filtrate was concentrated
  14. customto provide a residue
  15. customThe obtained residue was recrystallized with a mixed solution of chloroform and hexane, whereby 15 g of a powdery white solid of 4-(10-phenyl-9-anthryl)phenylboronic acid, which
  16. customthe object of the synthesis
  17. customwas obtained in a yield of 84% (synthesis scheme (a-5))

出典と根拠

ORDレコード
ord-1262bb8e26074f819a3410853f9c3a09
出典データセット
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08603644B2

反応ノート

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