Trimethylsilyl triflate → 1-[4-(Benzyloxy)-3-methylphenyl]-2-bromoethanone

HRID 920528

반응식

HRID 920528 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][C:10]=1[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.C1C(=O)N([Br:47])C(=O)C1>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH2:16][Br:47])=[CH:11][C:10]=1[CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 65367Trimethylsilyl triflateHCID 67184N-bromobutanimideHCID 81531DiisopropylethylamineHCID 12969325Ethanone, 1-[3-methyl-4-(phenylmethoxy)phenyl]-

생성물 1

HCID 129693271-[4-(Benzyloxy)-3-methylphenyl]-2-bromoethanone수율 70.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a solution of 1-(4-benzyloxy-3-methyl-phenyl)-ethanone (12.89 g; 53.1 mmol) in CH2Cl2 was added, dropwise, at 0° C., DIPEA (10.9 mL; 63.7 mmol) and trimethylsilyl trifluoromethanesulfonate (11.1 mL; 61.1 mmol). The resulting mixture was stirred at 0° C. for 1 hour, and subsequently, NBS (10.87 g; 61.1 mmol) was added in one portion. The mixture was allowed to warm to RT stirred overnight. Then the mixture was concentrated in vacuo, the residue dissolved in EtOAc, washed with water twice, and brine, dried (MgSO4), filtered, and concentrated in vacuo to afford 1-(4-benzyloxy-3-methyl-phenyl)-2-bromo-ethanone (11.90 g).

후처리

  1. customat 0° C.
  2. temperatureto warm to RT
  3. stirringstirred overnight
  4. concentrationThen the mixture was concentrated in vacuo
  5. dissolutionthe residue dissolved in EtOAc
  6. washwashed with water twice
  7. dry with materialbrine, dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-fe1b9589b55747c4ba87726a178f5938
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273017B2

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