Benzene, 4-bromo-1,2-dimethoxy- → 7-Benzyloxy-3-(4,5-dimethoxy-2-nitrophenyl)-1,2-dihydronaphthalene

HRID 1433933

Reaction equation

HRID 1433933 reaction equation
BrC1C=CC(OC)=C(OC)C=1.Br[C:13]1[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[CH:15][C:14]=1[N+:23]([O-:25])=[O:24].[CH2:26]([O:33][C:34]1[CH:43]=[C:42]2[C:37]([CH:38]=[C:39](Br)[CH2:40][CH2:41]2)=[CH:36][CH:35]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[CH2:26]([O:33][C:34]1[CH:43]=[C:42]2[C:37]([CH:38]=[C:39]([C:13]3[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[CH:15][C:14]=3[N+:23]([O-:25])=[O:24])[CH2:40][CH2:41]2)=[CH:36][CH:35]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

4

Reactant 3

HCID 76114Benzene, 4-bromo-1,2-dimethoxy-HCID 1709684-Bromo-5-nitroveratroleHCID 230874203-Bromo-1,2-dihydro-7-(phenylmethoxy)naphthalene

Product 1

HCID 230874267-Benzyloxy-3-(4,5-dimethoxy-2-nitrophenyl)-1,2-dihydronaphthaleneYield 21.8%

Procedure

Synthesized from 1-bromo-3,4-dimethoxybenzene according to an analogous synthetic method to Preparation Example 108, 1-bromo-4,5-dimethoxy-2-nitrobenzene (7.5 g) and 7-benzyloxy-3-bromo-1,2-dihydronaphthalene (4.5 g) were used according to an analogous synthetic method to Preparation Example 107 to provide 7-benzyloxy-3-(4,5-dimethoxy-2-nitrophenyl)-1,2-dihydronaphthalene (1.3 g). The total amount of this compound was used according to an analogous synthetic method to Example 30 to provide the title compound (822 mg).

Workup

  1. customwere used according to an analogous synthetic method to Preparation Example 107

Sources & evidence

ORD record
ord-c1bd0f8be5354add8b27466babec199f
Source dataset
uspto-grants-2009_11
Patent number
US07612114B2

Linked notes

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