Hydrochloric Acid → (4-Methoxy-2-{[(triisopropylsilyl)oxy]methyl}phenyl)boronic acid

HRID 1518248노트

반응식

HRID 1518248 반응식
Br[C:2]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:3]=1[CH2:4][O:5][Si:6]([CH:13]([CH3:15])[CH3:14])([CH:10]([CH3:12])[CH3:11])[CH:7]([CH3:9])[CH3:8].[Li]CCCC.[B:27](OC(C)C)([O:32]C(C)C)[O:28]C(C)C.Cl>C1COCC1>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:2]([B:27]([OH:32])[OH:28])=[C:3]([CH2:4][O:5][Si:6]([CH:13]([CH3:15])[CH3:14])([CH:10]([CH3:12])[CH3:11])[CH:7]([CH3:9])[CH3:8])[CH:16]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 67346559HCID 67346559, 화합물HCID 178418339Butyllithium

생성물 1

HCID 67345879(4-Methoxy-2-{[(triisopropylsilyl)oxy]methyl}phenyl)boronic acid수율 64%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

[(2-bromo-5-methoxybenzyl)oxy](triisopropyl)silane (1 eq.) was dissolved in anhydrous THF (0.43M solution) and the solution was cooled to −78° C. A solution of n-BuLi (1.6M in hexanes, 1.05 eq.) was added and the resulting mixture was left stirring for 1 h at −78° C. Then triisopropyl borate (50% in THF, 1.3 eq.) was added dropwise and the mixture was allowed to warm to RT overnight. 1N HCl was added and the resulting mixture was left stirring at RT for 30 min. THF was removed in vacuo and replaced with Et2O. The organic phase was washed with water and with brine, then dried over Na2SO4 and evaporated in vacuo. The product was obtained as a colorless oil (64% yield, 65% pure) which was used without further purification in the next reaction.

후처리

  1. waitthe resulting mixture was left
  2. temperatureto warm to RT overnight
  3. waitthe resulting mixture was left
  4. stirringstirring at RT for 30 min
  5. customTHF was removed in vacuo
  6. washThe organic phase was washed with water and with brine
  7. dry with materialdried over Na2SO4
  8. customevaporated in vacuo
  9. customThe product was obtained as a colorless oil (64% yield, 65% pure) which
  10. customwas used without further purification in the next reaction

출처 및 근거

ORD 기록
ord-6bd34ecbd1284eb5b8f2f0048d99f7dc
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232390B2

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