1-Bromo-2-methoxynaphthalene → 1-(5-Bromo-6-methoxynaphthalen-2-yl)ethan-1-one

HRID 1657535Notes

Reaction equation

HRID 1657535 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:12][CH3:13].[Cl:14][C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][C:16]=1[O:25][CH3:26].[F:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=[CH:30][C:29]=1[O:38][CH3:39]>>[Br:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[CH:9][C:8]([C:16](=[O:25])[CH3:15])=[CH:7]2.[Cl:14][C:15]1[C:16]([O:25][CH3:26])=[CH:17][CH:18]=[C:19]2[C:24]=1[CH:23]=[CH:22][C:21]([C:29](=[O:38])[CH3:28])=[CH:20]2.[F:27][C:28]1[C:29]([O:38][CH3:39])=[CH:30][CH:31]=[C:32]2[C:37]=1[CH:36]=[CH:35][C:34]([C:3](=[O:12])[CH3:2])=[CH:33]2

Participants

6

Reactant 3

HCID 728601-Bromo-2-methoxynaphthaleneHCID 115646231-Chloro-2-methoxynaphthaleneHCID 126561051-Fluoro-2-methoxynaphthalene

Product 3

HCID 6221781-(5-Bromo-6-methoxynaphthalen-2-yl)ethan-1-oneHCID 158904591-(5-Chloro-6-methoxynaphthalen-2-yl)ethan-1-oneHCID 21494953HCID 21494953, compound

Procedure

Repeating this procedure but replacing the nitrobenzene with dichloromethylene and replacing the β-naphthol methyl ether with 1-bromo-2-methoxynaphthalene, 1- chloro-2-methoxynaphthalene, and 1-fluoro-2-methoxynaphthalene -- 5-bromo-6-methoxy-2-acetylnaphthalene, 5-chloro-6-methoxy-2-acetylnaphthalene, and 5-fluoro-6-methoxy-2-acetylnaphthalene, respectively, were produced. A higher yield was obtained starting with the halo compounds, and less extensive processing was required to obtain a product having high purity.

Sources & evidence

ORD record
ord-b604e726bc3945d793293cedd01beb14
Source dataset
uspto-grants-1976_06
Patent number
US03960957

Reaction notes

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