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

HRID 2423690Notes

Reaction equation

HRID 2423690 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-60e100f4c8d5450982bd569c921907dd
Source dataset
uspto-grants-2011_06
Patent number
US07960412B2

Reaction notes

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