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

HRID 1465641Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1465641
[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]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 38532461-(2,6-difluoro-4-methoxyphenyl)ethanoneAusbeute 58,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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)+.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-976829f9bf664e168ca55fd2b2e55427
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999983B2

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