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

HRID 920528

反応式

HRID 920528 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fe1b9589b55747c4ba87726a178f5938
出典データセット
uspto-grants-2016_03
特許番号
US09273017B2

関連ノート

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