Sulfuric Acid → Ethyl 7-bromo-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate
Reaktionsgleichung
OS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[Br:20][C:21]1[CH:22]=[C:23]([C:27]([CH3:42])([CH3:41])[C:28]([CH:30]([C:36](OCC)=[O:37])[C:31]([O:33][CH2:34][CH3:35])=[O:32])=[O:29])[CH:24]=[CH:25][CH:26]=1>>[Br:20][C:21]1[CH:22]=[C:23]2[C:24]([C:36]([OH:37])=[C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:28](=[O:29])[C:27]2([CH3:41])[CH3:42])=[CH:25][CH:26]=1Komponenten
4
Versuchsvorschrift
H2SO4 (60 mL, 710 mmol) was cooled to 0° C. and treated with P2O5 (20 g, 141 mmol). The mixture was brought to room temperature and added to diethyl 2-(2-(3-bromophenyl)-2-methylpropanoyl)malonate (17.44 g, 45 mmol). The reaction mixture was then stirred for 2 hours. Ice (H2O) was added, and the aqueous mixture was extracted with EtOAc (3×). The combined organic layers were washed with water (2×) and brine, dried (MgSO4), and concentrated in vacuo to give the crude compound as an orange oil. The crude oil was purified by silica flash chromatography (0-100% DCM/hexane) to give the desired compound as a white solid (6.27 g). MS (m/e)=339.1 (M+H)+.
Aufarbeitung
- customwas brought to room temperature
- additionIce (H2O) was added
- extractionthe aqueous mixture was extracted with EtOAc (3×)
- washThe combined organic layers were washed with water (2×) and brine
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customto give the crude compound as an orange oil
- customThe crude oil was purified by silica flash chromatography (0-100% DCM/hexane)
Quellen und Nachweise
- ORD-Eintrag
- ord-9729967047bd4d7ab3750a5c9cf864b3
- Quelldatensatz
- uspto-grants-2009_12
- Patentnummer
- US07635715B2
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