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

HRID 1950088Notes

Reaction equation

HRID 1950088 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)[CH:32]=[C: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 230874972-(6-Methoxy-3,3-dimethyl-3,4-dihydronaphthalen-2-yl)phenylamineYield 53.5%

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 57 to provide the title compound (676 mg).

Sources & evidence

ORD record
ord-91431b1bdb2e40da9e69165d29a355f0
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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