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

HRID 1433901Notes

Reaction equation

HRID 1433901 reaction equation
BrC1C(C)(C)CC2C(C=1)=CC=C(OC)C=2.BrC1C=CC=CC=1[N+]([O-])=O.[CH3:26][O:27][C:28]1[CH:37]=[C:36]2[C:31]([CH:32]=[C:33]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=3[N+:46]([O-])=O)[C:34]([CH3:39])([CH3:38])[CH2:35]2)=[CH:30][CH:29]=1>>[CH3:26][O:27][C:28]1[CH:37]=[C:36]2[C:31](=[CH:30][CH:29]=1)[CH2:32][CH:33]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[NH2:46])[C:34]([CH3:39])([CH3:38])[CH2:35]2

Participants

4

Reactant 3

HCID 113411-Bromo-2-nitrobenzeneHCID 230875527-Methoxy-2,2-dimethyl-3-(2-nitrophenyl)-1,2-dihydronaphthaleneHCID 230875703-Bromo-7-methoxy-2,2-dimethyl-1,2-dihydronaphthalene

Product 1

HCID 230874012-(6-Methoxy-3,3-dimethyl-1,2,3,4-tetrahydronaphthalen-2-yl)phenylamineYield 74.4%

Procedure

Synthesized from 3-bromo-7-methoxy-2,2-dimethyl-1,2-dihydronaphthalene and 1-bromo-2-nitrobenzene according to an analogous synthetic method to Preparation Example 107 described below, 7-methoxy-2,2-dimethyl-3-(2-nitrophenyl)-1,2-dihydronaphthalene (1.4 g) was used according to an analogous synthetic method to Example 30 to provide the title compound (948 mg).

Sources & evidence

ORD record
ord-f48ad267f1814997b7cea87dffb8abfb
Source dataset
uspto-grants-2009_11
Patent number
US07612114B2

Reaction notes

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