2-Bromo-4-methoxy-1-nitrobenzene → 6-(2-Amino-5-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950118Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1950118
C(OC1C=C2C(C=C(Br)CC2)=CC=1)C1C=CC=CC=1.BrC1C=C(OC)C=CC=1[N+]([O-])=O.C([O:39][C:40]1[CH:49]=[C:48]2[C:43]([CH:44]=[C:45]([C:50]3[CH:55]=[C:54]([O:56][CH3:57])[CH:53]=[CH:52][C:51]=3[N+:58]([O-])=O)[CH2:46][CH2:47]2)=[CH:42][CH:41]=1)C1C=CC=CC=1>>[NH2:58][C:51]1[CH:52]=[CH:53][C:54]([O:56][CH3:57])=[CH:55][C:50]=1[CH:45]1[CH2:46][CH2:47][C:48]2[CH:49]=[C:40]([OH:39])[CH:41]=[CH:42][C:43]=2[CH2:44]1

Komponenten

4

Edukt 3

HCID 129667452-Bromo-4-methoxy-1-nitrobenzeneHCID 230874107-Benzyloxy-3-(5-methoxy-2-nitrophenyl)-1,2-dihydronaphthaleneHCID 230874203-Bromo-1,2-dihydro-7-(phenylmethoxy)naphthalene

Produkt 1

HCID 230871806-(2-Amino-5-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-olAusbeute 67,7 %

Versuchsvorschrift

To a solution of 3-bromo-4-nitrophenol (4.1 g) in N,N-dimethylformamide (40 ml) were sequentially added cesium carbonate (9.2 g) and methyl iodide (1.5 ml), and the solution was stirred overnight at room temperature. Water was added thereto, the solution was stirred, extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide 2-bromo-4-methoxy-1-nitrobenzene (4.1 g). Synthesized from 7-benzyloxy-3-bromo-1,2-dihydronaphthalene and 2-bromo-4-methoxy-1-nitrobenzene according to an analogous synthetic method to Preparation Example 107, 7-benzyloxy-3-(5-methoxy-2-nitrophenyl)-1,2-dihydronaphthalene (3.4 g) was used according to an analogous synthetic method to Example 30 to provide the title compound (1.6 g).

Quellen und Nachweise

ORD-Eintrag
ord-573c0fb2e23c4cb8bf4e0aa4807e8036
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399520B2

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