1,4-Benzodioxan → Methanone, (2-bromo-5-iodophenyl)(2,3-dihydro-1,4-benzodioxin-6-yl)-
Reaktionsgleichung
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[O:12]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][CH2:14][CH2:13]1.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([C:20]1[CH:19]=[CH:18][C:17]2[O:12][CH2:13][CH2:14][O:15][C:16]=2[CH:21]=1)=[O:5]Komponenten
Versuchsvorschrift
To a stirred solution of 2-bromo-5-iodo-benzoyl chloride (26.4 g, 76.56 mmol) in dichloromethane (250 mL) was added benzo(1,4)-dioxane (10.41 g, 76.26 mmol) at 0° C. To this reaction mixture, AlCl3 (40.78 g, 305.47 mmol) was added in portions. After stirring overnight at room temperature, the reaction mixture was poured into crushed ice. The resulting mixture was extracted with dichloromethane (500 mL×2). The dichloromethane layers were combined and washed with water (200 mL), saturated aqueous sodium bicarbonate solution (200 mL×2), and brine (200 mL), then dried over sodium sulfate and concentrated. The solid product was triturated with hexanes, and the triturated product was dried under vacuum to furnish (2-bromo-5-iodo-phenyl)-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-methanone (30 g).
Aufarbeitung
- additionthe reaction mixture was poured
- custominto crushed ice
- extractionThe resulting mixture was extracted with dichloromethane (500 mL×2)
- washwashed with water (200 mL), saturated aqueous sodium bicarbonate solution (200 mL×2), and brine (200 mL)
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customThe solid product was triturated with hexanes
- customthe triturated product was dried under vacuum
Quellen und Nachweise
- ORD-Eintrag
- ord-bf29f2e62f324d66bd4cf2029aafc6d2
- Quelldatensatz
- uspto-grants-2013_06
- Patentnummer
- US08466114B2
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