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

HRID 1054702ノート

反応式

HRID 1054702 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-e58c053165154d4caa095b5cc1dc77a2
出典データセット
uspto-grants-2016_07
特許番号
US09394285B2

反応ノート

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