1-Bromo-3,4-(methylenedioxy)benzene → 5-(6-Benzyloxy-3,4-dihydronaphthalen-2-yl)-6-nitrobenzo[1,3]dioxole

HRID 1433934Notes

Reaction equation

HRID 1433934 reaction equation
BrC1C=CC2OCOC=2C=1.Br[C:12]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:15]2[O:16][CH2:17][O:18][C:14]=2[CH:13]=1.[CH2:24]([O:31][C:32]1[CH:41]=[C:40]2[C:35]([CH:36]=[C:37](Br)[CH2:38][CH2:39]2)=[CH:34][CH:33]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH2:24]([O:31][C:32]1[CH:41]=[C:40]2[C:35](=[CH:34][CH:33]=1)[CH:36]=[C:37]([C:12]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:15]3[O:16][CH2:17][O:18][C:14]=3[CH:13]=1)[CH2:38][CH2:39]2)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 3

HCID 758311-Bromo-3,4-(methylenedioxy)benzeneHCID 15197565-Bromo-6-nitro-1,3-benzodioxoleHCID 230874203-Bromo-1,2-dihydro-7-(phenylmethoxy)naphthalene

Product 1

HCID 666270645-(6-Benzyloxy-3,4-dihydronaphthalen-2-yl)-6-nitrobenzo[1,3]dioxoleYield 10.9%

Procedure

Synthesized from 4-bromo-1,2-(methylenedioxy)benzene according to an analogous synthetic method to Preparation Example 108, 5-bromo-6-nitrobenzo[1,3]dioxole (9.4 g) and 7-benzyloxy-3-bromo-1,2-dihydronaphthalene (6.0 g) were used according to an analogous synthetic method to Preparation Example 107 to provide the title compound (834 mg).

Workup

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

Sources & evidence

ORD record
ord-42b916031730460c8d9110e99a1ab3c5
Source dataset
uspto-grants-2009_11
Patent number
US07612114B2

Reaction notes

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