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

HRID 1950120Notes

Reaction equation

HRID 1950120 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-3f0e7b19157640ad9eb69707ada8842e
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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