Acetone → 2-(4-Bromo-2-methoxyphenyl)propan-2-ol

HRID 1054702노트

반응식

HRID 1054702 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([O:8][CH3:9])[CH:7]=1.[CH3:11][C:12]([CH3:14])=[O:13].[Li]CCCC>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]([OH:13])([CH3:14])[CH3:11])=[C:6]([O:8][CH3:9])[CH:7]=1

참가 물질

5

반응물 3

HCID 180AcetoneHCID 468357314-Bromo-1-iodo-2-methoxybenzeneHCID 178418339Butyllithium

생성물 1

HCID 866987012-(4-Bromo-2-methoxyphenyl)propan-2-ol수율 25.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 5-bromo-2-iodoanisole (668 mg, 2.14 mmol) and acetone (0.471 mL, 6.40 mmol) in tetrahydrofuran (7.62 mL) at −78° C. was added n-BuLi (2.5M in hexane, 0.940 mL, 2.35 mmol) in a dropwise manner. The reaction mixture was stirred at −78° C. for 2 hours. The reaction mixture was quenched with saturated aqueous ammonium chloride, warmed to room temperature and extracted with ethyl acetate (2×). The combined organic layers were dried over magnesium sulfate and filtered, and concentrated under reduced pressure yielding 680 mg of crude oil. Purification by column chromatography (0-10% ethyl acetate/heptanes) afforded the title compound (133 mg, 25% yield) as a clear, colorless oil. MS (ES+) 226.9 (M−H2O+H)+. 1H NMR (400 MHz, CDCl3) δ: 7.20 (d, 1H), 7.06-7.10 (m, 1H), 7.04 (d, 1H), 3.91 (s, 3H), 1.58 (s, 6H).

후처리

  1. customThe reaction mixture was quenched with saturated aqueous ammonium chloride
  2. temperaturewarmed to room temperature
  3. extractionextracted with ethyl acetate (2×)
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customyielding 680 mg of crude oil
  8. customPurification by column chromatography (0-10% ethyl acetate/heptanes)

출처 및 근거

ORD 기록
ord-e58c053165154d4caa095b5cc1dc77a2
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394285B2

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