Ammonium Chloride → 2-Benzyloxy-1-methoxybenzeneboronic acid

HRID 2247436

반응식

HRID 2247436 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[C:13](Br)[CH:12]=[CH:11][C:10]=1[O:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[B:23](OOC(C)C)([O:29]OC(C)C)[O:24]OC(C)C.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH2:1]([O:8][CH:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1([O:16][CH3:17])[B:23]([OH:29])[OH:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 149128522-(Benzyloxy)-4-bromo-1-methoxybenzeneHCID 53683132Triisopropoxy borateHCID 178418339Butyllithium

생성물 1

HCID 686332012-Benzyloxy-1-methoxybenzeneboronic acid

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

4.86 g of 2-Benzyloxy-4-bromo-1-methoxybenzene was dissolved in 100 ml of anhydrous tetrahydrofuran and cooled to −78° C. in a nitrogen atmosphere. 15 ml of 1.6 M n-butyl lithium in hexane was added dropwise, and the mixture was stirred for 30 minutes. 6 ml of Triisopropoxy borate was added all at once, and the mixture was allowed to warm overnight at room temperature. A saturated aqueous ammonium chloride solution was added to the reaction mixture which was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated. The residue was dissolved in 1N aqueous sodium hydroxide and extracted with diethyl ether. The aqueous layer was neutralized with 5N hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated to give 1.76 of the title compound.

후처리

  1. temperatureto warm overnight at room temperature
  2. extractionwas then extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. dissolutionThe residue was dissolved in 1N aqueous sodium hydroxide
  7. extractionextracted with diethyl ether
  8. extractionextracted with ethyl acetate
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. concentrationthe filtrate was concentrated

출처 및 근거

ORD 기록
ord-4a6fe16e71db4bb9aadec937a1c77734
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07687664B2

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