6-Nitro-1,3-benzodioxol-5-ol → Methyl 5-bromo-2-(4,5-methylenedioxy-2-nitrophenoxy)valerate
Reaction equation
[CH2:1]1[O:9][C:8]2[C:3](=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([OH:10])[CH:7]=2)[O:2]1.Br[CH:15]([CH2:20][CH2:21][CH2:22][Br:23])[C:16]([O:18][CH3:19])=[O:17]>>[Br:23][CH2:22][CH2:21][CH2:20][CH:15]([O:10][C:6]1[CH:7]=[C:8]2[O:9][CH2:1][O:2][C:3]2=[CH:4][C:5]=1[N+:11]([O-:13])=[O:12])[C:16]([O:18][CH3:19])=[O:17]Participants
3
Procedure
In a manner similar to that of Reference Example 5, 4,5-methylenedioxy-2-nitrophenol was allowed to react with methyl 2,5-dibromovalerate to give methyl 5-bromo-2-(4,5-methylenedioxy-2-nitrophenoxy)valerate, which was then allowed to react, in a manner similar to that of Reference Example 8, with 1-(4-fluorophenyl)piperazine to obtain methyl 5-[4-(4-fluorophenyl)-1-piperazinyl]-2-(4,5-methylenedioxy-2-nitrophenoxy)valerate as crystals, m.p. 98°-99° C. The overall yield was 15.6%.
Sources & evidence
- ORD record
- ord-52b19309adaa4a81b7cc29f3a7fff1d9
- Source dataset
- uspto-grants-1988_12
- Patent number
- US04789675
Reaction notes
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