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

HRID 2423691Notes

Reaction equation

HRID 2423691 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-242fb9f91ddf43f28081a8c584d90d66
Source dataset
uspto-grants-2011_06
Patent number
US07960412B2

Reaction notes

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