Acetyl chloride → 1-(2,6-difluoro-4-methoxyphenyl)ethanone

HRID 1465641노트

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HRID 1465641 반응식
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[F:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]([F:18])[CH:11]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]([F:18])[C:11]=1[C:5](=[O:7])[CH3:6]

참가 물질

6

반응물 4

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 27245183,5-DifluoroanisoleHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 38532461-(2,6-difluoro-4-methoxyphenyl)ethanone수율 58.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

A mixture of aluminium chloride (10.0-15 g, 69.4 mmol, 5.0 equiv) and acetyl chloride (2.0 mL, 28 mmol, 2.0 equiv) in CH2Cl2 (50.0 mL) was stirred at 0° C. for 30 min. The reaction mixture was slowly added with 1,3-difluoro-5-methoxy-benzene (2.0 g, 13.9 mmol, 1.0 equiv) in CH2Cl2 (10.0 mL), and the resultant solution was stirred at room temperature for additional 2.0 h. The solution was basified with saturated aqueous NaHCO3 (20 mL) to pH 8-9. The organic layer was separated, dried over MgSO4(s), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (15% EtOAc in hexanes as eluant) to give 1-(2,6-difluoro-4-methoxyphenyl)ethanone (1.5 g, 8.1 mmol) as yellow oil in 58% yield: 1H NMR (CDCl3, 500 MHz) δ 6.46-6.48 (m, 2 H), 3.83 (s, 3 H), 2.56 (s, 3 H); ESI-MS: m/z 187.0 (M+H)+.

후처리

  1. customThe organic layer was separated
  2. dry with materialdried over MgSO4(s)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (15% EtOAc in hexanes as eluant)

출처 및 근거

ORD 기록
ord-976829f9bf664e168ca55fd2b2e55427
출처 데이터셋
uspto-grants-2015_04
특허 번호
US08999983B2

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