Methyl iodide → Ethyl 2-(4-bromophenyl)propanoate

HRID 553682ノート

反応式

HRID 553682 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[CH3:14][Si]([N-][Si](C)(C)C)(C)C.[Li+].IC>C1COCC1>[CH2:12]([O:11][C:9](=[O:10])[CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[CH3:14])[CH3:13]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 7020609Ethyl 2-(4-bromophenyl)acetate

生成物 1

HCID 13840376Ethyl 2-(4-bromophenyl)propanoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To ethyl 4-bromophenylacetate (2.137 g, 8.8 mmol) in THF (20 mL) at −78° C. was added lithium bis(trimethylsilyl)amide (1M in hexane; 11.4 mL, 11.4 mmol), and the solution was stirred for 1 hour at −78° C. Iodomethane (0.71 mL, 11.4 mmol) in THF (5 mL) was added, and the reaction was warmed to room temperature. The mixture was quenched with water and concentrated. The residue was dissolved in EtOAc and washed three times with water and once with brine. The organic layer was dried and concentrated, and the crude material was purified by silica gel chromatography (0-60% EtOAc in hexanes) to give 2-(4-bromo-phenyl)-propionic acid ethyl ester.

後処理

  1. temperaturethe reaction was warmed to room temperature
  2. customThe mixture was quenched with water
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed three times with water
  6. customThe organic layer was dried
  7. concentrationconcentrated
  8. customthe crude material was purified by silica gel chromatography (0-60% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-c0b7bf1678a842dab93e77500fab5897
出典データセット
uspto-grants-2011_11
特許番号
US08048902B2

反応ノート

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