2-Fluoroanisole → 4-(3-Fluoro-4-methoxy-benzoyl)-benzoic acid methyl ester

HRID 2100147

Reaktionsgleichung

Reaktionsgleichung von HRID 2100147
[Al+3].[Cl-].[Cl-].[Cl-].[CH3:5][O:6][C:7](=[O:17])[C:8]1[CH:13]=[CH:12][C:11]([C:14](Cl)=[O:15])=[CH:10][CH:9]=1.[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH3:26]>ClCCl>[CH3:5][O:6][C:7](=[O:17])[C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:15])[C:23]2[CH:22]=[CH:21][C:20]([O:25][CH3:26])=[C:19]([F:18])[CH:24]=2)=[CH:10][CH:9]=1

Komponenten

5

Edukt 3

HCID 675762-FluoroanisoleHCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 686545474-(3-Fluoro-4-methoxy-benzoyl)-benzoic acid methyl esterAusbeute 17,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

To an ice-cooled slurry of AlCl3 (2.01 g, 15.1 mmol) in dichloromethane (10 mL) was slowly added 4-chlorocarbonyl-benzoic acid methyl ester (2 g, 10.1 mmol) in dichloromethane (5 mL). The reaction mixture was stirred for 20 min in the ice bath then 2-fluoroanisole (1.4 mL, 12.1 mmol) in dichloromethane (5 mL) was added. The reaction mixture was stirred at room temperature for 20 h. The reaction mixture was poured into ice cold 1 N HCl (10 mL) and the mixture was stirred for 15 min. The reaction mixture was transferred to a separatory funnel and the layers were separated. The aqueous layer was extracted with dichloromethane and the organic extracts were combined, washed with brine, dried over Na2SO4, filtered and concentrated. The crude solid was triturated with hot hexanes, filtered and washed with hexanes to give 0.5 g (17%) of compound 173 as a white powder. 1H NMR (400 MHz, DMSO-d6): δ 3.89 (s, 3 H), 3.94 (s, 3 H), 7.32 (t, J=8.5 Hz, 1 H), 7.57 (d, J=8.8 Hz, 1 H), 7.59-7.63 (m, 1 H), 7.81 (d, J=8.2 Hz, 2 H), 8.04 (s, 1 H), 8.10 (d, J=8.3 Hz, 2 H).

Aufarbeitung

  1. stirringthe mixture was stirred for 15 min
  2. customThe reaction mixture was transferred to a separatory funnel
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with dichloromethane
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude solid was triturated with hot hexanes
  10. filtrationfiltered
  11. washwashed with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-e4a9992d4aea416982d885270cb9e76f
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07569601B2

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