6-Methoxy-alpha-tetralone → 7-Methoxy-3-(2-methyl-6-nitrophenyl)-1,2-dihydronaphthalene

HRID 1950122Notes

Reaction equation

HRID 1950122 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=O)[CH2:8][CH2:7][CH2:6]2.BrC1CCC2C(C=1)=CC=C(OC)C=2.Br[C:28]1[C:33]([N+:34]([O-:36])=[O:35])=[CH:32][CH:31]=[CH:30][C:29]=1[CH3:37]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10]([CH:9]=[C:8]([C:28]3[C:33]([N+:34]([O-:36])=[O:35])=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:37])[CH2:7][CH2:6]2)=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 141126-Methoxy-alpha-tetraloneHCID 2318282-Bromo-3-nitrotolueneHCID 116011473-Bromo-7-methoxy-1,2-dihydronaphthalene

Product 1

HCID 230872677-Methoxy-3-(2-methyl-6-nitrophenyl)-1,2-dihydronaphthalene

Procedure

Synthesized from 6-methoxy-1-tetralone according to an analogous synthetic method to Preparation Example 106, 3-bromo-7-methoxy-1,2-dihydronaphthalene (2.7 g) and 2-bromo-3-nitrotoluene (4.8 g) were used according to an analogous synthetic method to Preparation Example 107 to provide 7-methoxy-3-(2-methyl-6-nitrophenyl)-1,2-dihydronaphthalene (925 mg). This compound (920 mg) was used according to an analogous synthetic method to Example 30 to provide the title compound (740 mg).

Workup

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

Sources & evidence

ORD record
ord-35c1cbcb75c54cbc9bbce3a2ce66e5b4
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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