Pyridinium chloride → 3-Bromo-7,9-dihydroxy-10,11-dihydrodibenz[b,f]oxepin-10-one
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][C:10](=[O:12])[C:9]3[C:13]([O:19]C)=[CH:14][C:15]([O:17]C)=[CH:16][C:8]=3[O:7][C:6]=2[CH:21]=1.Cl.N1C=CC=CC=1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][C:10](=[O:12])[C:9]3[C:13]([OH:19])=[CH:14][C:15]([OH:17])=[CH:16][C:8]=3[O:7][C:6]=2[CH:21]=1Participants
Conditions
- Temperature
- 195 °C
Procedure
To 395 mg (F.W. 349.18, 15.75 mmol) of dimethoxylated compound (27) was added 2.0 g of pyridine hydrochloride and stirred at 195° C. for 1.5 hours and then, ice water was slowly added thereto. The resulting solution was extracted with ethyl acetate and the extract was washed with 1N hydrochloric acid, water and a saturated sodium chloride aqueous solution in the order named. The extract thus washed was dried with anhydrous magnesium sulfate and then, concentrated. The residue was purified by silica gel column chromatography (developing solvent; ethyl acetate:hexane=1:2). Furthermore, the product thus obtained was recrystallized from dioxane and dioxane-hexane to obtain 223 mg (61%) of the title compound. (TLC; ethyl acetate:hexane=1:2).
Workup
- extractionThe resulting solution was extracted with ethyl acetate
- washthe extract was washed with 1N hydrochloric acid, water
- extractionThe extract thus
- washwashed
- dry with materialwas dried with anhydrous magnesium sulfate
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography (developing solvent; ethyl acetate:hexane=1:2)
- customFurthermore, the product thus obtained
- customwas recrystallized from dioxane and dioxane-hexane
Sources & evidence
- ORD record
- ord-a6bd1dbfe2cf47208cf77a82dcc98ff6
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06602898B1
Reaction notes
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