4-Bromo-3-nitrobenzotrifluoride → 7-Methoxy-3-(2-nitro-4-trifluoromethylphenyl)-1,2-dihydronaphthalene

HRID 1950054Notes

Reaction equation

HRID 1950054 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C([Sn](CCCC)(CCCC)C1C=CC(C(F)(F)F)=CC=1[N+]([O-])=O)CCC.FC(F)(F)S(O[C:47]1[CH2:56][CH2:55][C:54]2[C:49](=[CH:50][CH:51]=[C:52]([O:57][CH3:58])[CH:53]=2)[CH:48]=1)(=O)=O>>[CH3:58][O:57][C:52]1[CH:53]=[C:54]2[C:49]([CH:48]=[C:47]([C:2]3[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=3[N+:12]([O-:14])=[O:13])[CH2:56][CH2:55]2)=[CH:50][CH:51]=1

Participants

4

Reactant 3

HCID 5207064-Bromo-3-nitrobenzotrifluorideHCID 153302566-Methoxy-3,4-dihydronaphthalen-2-yl trifluoromethanesulfonateHCID 23087363Tributyl(2-nitro-4-trifluoromethylphenyl)tin

Product 1

HCID 230874677-Methoxy-3-(2-nitro-4-trifluoromethylphenyl)-1,2-dihydronaphthalene

Procedure

Synthesized from 1-bromo-2-nitro-4-trifluoromethylbenzene according to an analogous synthetic method to Preparation Example 76, tributyl(2-nitro-4-trifluoromethylphenyl)tin (7.4 and 6-methoxy-3,4-dihydronaphthalen-2-yl trifluoromethanesulfonate (2.2 g) were used according to an analogous synthetic method to Preparation Example 77 to provide 7-methoxy-3-(2-nitro-4-trifluoromethylphenyl)-1,2-dihydronaphthalene (1.5 g). The total amount of this compound was used according to an analogous synthetic method to Example 30 to provide the title compound (1.0 g).

Workup

  1. customwere used according to an analogous synthetic method to Preparation Example 77

Sources & evidence

ORD record
ord-15450e0bc8a347469a785d37576e52e6
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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