Hydrochloric Acid → 9-Anthraceneboronic Acid

HRID 646646ノート

反応式

HRID 646646 の反応式
[Li]C(CC)C.Br[C:7]1[C:8]2[C:13]([CH:14]=[C:15]3[C:20]=1[CH:19]=[CH:18][CH:17]=[CH:16]3)=[CH:12][CH:11]=[CH:10][CH:9]=2.C([O:24][B:25](OC(C)C)[O:26]C(C)C)(C)C.Cl>CCOCC.CO>[CH:19]1[C:20]2[C:15](=[CH:14][C:13]3[C:8]([C:7]=2[B:25]([OH:26])[OH:24])=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:16]=[CH:17][CH:18]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 740629-BromoanthraceneHCID 178418400CID 53628100

生成物 1

HCID 155102139-Anthraceneboronic Acid収率 94.6%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 3283Diethyl Ether溶媒

実験手順

sec-BuLi (4.3 mL, 6.0 mmol, 1.4M solution in cyclohexane) was added dropwise to a solution of 9-bromoanthracene (1.29 g, 5.0 mmol) in Et2O (20 mL) at 0° C. under N2. The reaction was held at 0° C. for 15 minutes then warmed to rt and stirred an additional 45 minutes. Triisopropylborate (1.5 mL, 6.5 mmol) was added and the reaction was stirred at rt for 18 h. Concentrated HCl (1.0 mL) and MeOH (1.0 mL) was added and the reaction was stirred for 30 minutes. The layers were separated and the aqueous phase was extracted three times with CH2Cl2. The combined organic layers were washed with H2O, sat. NaHCO3 (aq.), brine, and then dried over Na2SO4. Filtration and concentration gave 1.05 g of 9-anthraceneboronic acid.

後処理

  1. stirringthe reaction was stirred at rt for 18 h
  2. stirringthe reaction was stirred for 30 minutes
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted three times with CH2Cl2
  5. washThe combined organic layers were washed with H2O, sat. NaHCO3 (aq.), brine
  6. dry with materialdried over Na2SO4
  7. filtrationFiltration and concentration

出典と根拠

ORDレコード
ord-76ed8c58e15e49f0905b210d980324c6
出典データセット
uspto-grants-2010_04
特許番号
US07705157B2

反応ノート

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