Reaktionsgleichung
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([OH:11])=[C:6]([Cl:12])[CH:5]=1.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:5]=[C:6]([Cl:12])[C:7]([O:11][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:8]([Cl:10])[CH:9]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A mixture of 3,5-dichloro-4-hydroxy benzoic acid methyl ester (5.525 g, 25 mmol), benzyl bromide (5.13 g, 30 mmol) and potassium carbonate (6.91 g, 50 mmol) in N,N-dimethylformamide (100 mL) was stirred overnight at room temperature. The reaction mixture was poured into crushed ice (ca. 300 g) and the product was extracted with ethyl acetate (2×100 mL). The combined organic layers were dried over sodium sulphate and concentrated under reduced pressure. The solid residue was recrystallised from ethyl acetate and hexane. Yield: 7.47 g (96%) fine white needles. 1H-NMR (400 MHz, CDCl3) δ=3.93 (s, 3H, —OCH3), 5.12 (s, 2H, —CH2Ph), 7.35-7.44 (m, 3H), 7.54-7.58 (m, 2H), 8.01 (s, 2H). 13C-NMR (100 MHz, CDCl3) δ=52.66, 75.12, 127.18, 128.41, 128.48, 129.79, 130.13, 135.57, 154.57, 164.39.
Aufarbeitung
- additionThe reaction mixture was poured
- extractionthe product was extracted with ethyl acetate (2×100 mL)
- dry with materialThe combined organic layers were dried over sodium sulphate
- concentrationconcentrated under reduced pressure
- customThe solid residue was recrystallised from ethyl acetate and hexane
Quellen und Nachweise
- ORD-Eintrag
- ord-4bd4658cee4f43209c3530be92471ebb
- Quelldatensatz
- uspto-grants-2010_06
- Patentnummer
- US07745472B2
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