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

HRID 553682노트

반응식

HRID 553682 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 13840376Ethyl 2-(4-bromophenyl)propanoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c0b7bf1678a842dab93e77500fab5897
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08048902B2

반응 노트

불러오는 중…