N-Methylallylamine → 3-(4-Bromo-phenyl)-benzo[b]thiophen-6-ol

HRID 342197Notes

Reaction equation

HRID 342197 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:10]=3[S:11][CH:12]=2)=[CH:4][CH:3]=1.[Br:19]/[CH:20]=[CH:21]/[CH2:22][CH2:23]Br.[CH2:25]([NH:28][CH3:29])[CH:26]=[CH2:27]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][C:10]=3[S:11][CH:12]=2)=[CH:4][CH:3]=1.[Br:19][CH2:20]/[CH:21]=[CH:22]/[CH2:18][O:17][C:14]1[CH:15]=[CH:16][C:9]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=3)=[CH:12][S:11][C:10]=2[CH:13]=1.[CH2:21]([N:28]([CH2:25]/[CH:26]=[CH:27]/[CH2:18][O:17][C:14]1[CH:15]=[CH:16][C:9]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=3)=[CH:12][S:11][C:10]=2[CH:13]=1)[CH3:29])[CH:22]=[CH2:23]

Participants

6

Reactant 3

HCID 69391N-MethylallylamineHCID 14316427(1E)-1,4-dibromobut-1-eneHCID 154226413-(4-Bromophenyl)-6-methoxybenzo[b]thiophene

Product 3

HCID 179328883-(4-Bromo-phenyl)-benzo[b]thiophen-6-olHCID 44306432N-allyl-4-(3-(4-bromophenyl)benzo[b]thiophen-6-yloxy)-N-methylbut-2-en-1-aminiumHCID 677648196-(4-(E)-bromo-but-2-enyloxy)-3-(4-bromo-phenyl)-benzo[b]thiophene

Procedure

Analogously to Example 3, from 3-(4-bromo-phenyl)-6-methoxy-benzo[b]thiophene (Ex. 3b), after cleavage of the methoxy protecting group, reaction with (E)-1,4-dibromobutene and N-allyl-methyl-amine and salt formation, via 3-(4-bromo-phenyl)-benzo[b]thiophen-6-ol und via 6-(4-(E)-bromo-but-2-enyloxy)-3-(4-bromo-phenyl)-benzo[b]thiophene there is obtained (E)-allyl-[4-[3(4-bromo-phenyl)-benzo[b]thiopen-6-yloxy]-but-2-enyl]-methyl-amine.fumarat (1:1), MS: m/e 428 (M+H+, Br).

Sources & evidence

ORD record
ord-059ab091758d4d13bf30da96d258b7c2
Source dataset
uspto-grants-1999_01
Patent number
US05856503

Reaction notes

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