4-Bromo-3-nitroanisole → 5-Methoxy-2-(6-methoxy-3,3-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamine

HRID 1433899Notes

Reaction equation

HRID 1433899 reaction equation
BrC1C(C)(C)CC2C(C=1)=CC=C(OC)C=2.BrC1C=CC(OC)=CC=1[N+]([O-])=O.[CH3:28][O:29][C:30]1[CH:39]=[C:38]2[C:33]([CH:34]=[C:35]([C:42]3[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][C:43]=3[N+:50]([O-])=O)[C:36]([CH3:41])([CH3:40])[CH2:37]2)=[CH:32][CH:31]=1>>[CH3:49][O:48][C:45]1[CH:46]=[CH:47][C:42]([CH:35]2[C:36]([CH3:40])([CH3:41])[CH2:37][C:38]3[C:33](=[CH:32][CH:31]=[C:30]([O:29][CH3:28])[CH:39]=3)[CH2:34]2)=[C:43]([NH2:50])[CH:44]=1

Participants

4

Reactant 3

HCID 792884-Bromo-3-nitroanisoleHCID 230874327-Methoxy-3-(4-methoxy-2-nitrophenyl)-2,2-dimethyl-1,2-dihydronaphthaleneHCID 230875703-Bromo-7-methoxy-2,2-dimethyl-1,2-dihydronaphthalene

Product 1

HCID 230871355-Methoxy-2-(6-methoxy-3,3-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamineYield 86%

Procedure

Synthesized from 3-bromo-7-methoxy-2,2-dimethyl-1,2-dihydronaphthalene and 4-bromo-3-nitroanisole according to an analogous synthetic method to Preparation Example 107 described below, 7-methoxy-3-(4-methoxy-2-nitrophenyl)-2,2-dimethyl-1,2-dihydronaphthalene (1.9 g) was used according to an analogous synthetic method to Example 30 to provide the title compound (1.5 g).

Sources & evidence

ORD record
ord-e8b6905be4034c2fbc73b00a69dfb8a0
Source dataset
uspto-grants-2009_11
Patent number
US07612114B2

Reaction notes

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