Anisole → 3-(4-Fluorophenyl)-1-(4-methoxyphenyl)propan-1-one

HRID 556053

Reaktionsgleichung

Reaktionsgleichung von HRID 556053
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](Cl)=[O:11])=[CH:4][CH:3]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>[Al+3].[Cl-].[Cl-].[Cl-]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([C:18]2[CH:19]=[CH:20][C:15]([O:14][CH3:13])=[CH:16][CH:17]=2)=[O:11])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 7519AnisoleHCID 219642583-(4-Fluorophenyl)propionyl chloride

Produkt 1

HCID 115869503-(4-Fluorophenyl)-1-(4-methoxyphenyl)propan-1-oneAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6451240Aluminum(III) ChlorideKatalysator

Versuchsvorschrift

A procedure similar to step 2 of Example 1 was used. 3-(4-fluoro-phenyl)-propionyl chloride prepared in the step 1 and methylphenyl ether were used as starting materials, and anhydrous AlCl3 was used as catalyst. The obtained product was a white solid in a yield of 100%, mp: 80-81 └. 1H-NMR (CDCl3, 400 MHz) δ: 3.05 (2H, t, J=7.84 Hz, ArH), 3.23 (2H, t, J=7.84 Hz, ArH), 3.87 (3H, s, OCH3), 6.92 (2H, d, J=8.68 Hz, ArH), 6.97 (2H, t, 3JFH=3JHH=8.72 Hz, ArH), 7.21 (2H, dd, 3JHH=8.68 Hz, 4JFH=5.60 Hz, ArH), 7.93 (2H, d, J=8.68 Hz, ArH); EI-MS m/e (%): 258.0 (M+, 27), 135.0 (100).

Quellen und Nachweise

ORD-Eintrag
ord-2fa8761d4e77463bade1ef190eb68d7c
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08053581B2

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