3-Nitro-5,6,7,8-tetrahydronaphthalen-2-ol → Methyl 6-bromo-2-(5,6,7,8-tetrahydro-3-nitro-2-naphthyloxy)hexanoate
Reaction equation
[N+:1]([C:4]1[C:5]([OH:14])=[CH:6][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:12]=2[CH:13]=1)([O-:3])=[O:2].Br[CH:16]([CH2:21][CH2:22][CH2:23][CH2:24][Br:25])[C:17]([O:19][CH3:20])=[O:18]>>[Br:25][CH2:24][CH2:23][CH2:22][CH2:21][CH:16]([O:14][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:13][C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[CH:6]=1)[C:17]([O:19][CH3:20])=[O:18]Participants
3
Procedure
In a manner similar to that of Reference Example 5, 5,6,7,8-tetrahydro-3-nitro-2-naphthol was allowed to react with methyl 2,6-dibromohexanoate to give methyl 6-bromo-2-(5,6,7,8-tetrahydro-3-nitro-2-naphthyloxy)hexanoate as an oily product, which was then allowed to react, in a manner similar to that of Reference Example 8, with 1-(4-fluorophenyl)piperadine to obtain methyl 6-[4-(4-fluorophenyl)-1-piperazinyl]-2-(5,6,7,8-tetrahydro-3-nitro-2-naphthyloxy) hexanoate as an oily product. The overall yield was 79.4%.
Sources & evidence
- ORD record
- ord-d7aebe2ead1b45ba9b6ad2ed556da0ad
- Source dataset
- uspto-grants-1988_12
- Patent number
- US04789675
Reaction notes
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