1,6-Dibromohexane → Allyl-[6-[3-(4-bromo-phenyl)-benzo[b]thiophen-6-yloxy]-hexyl]methyl-amine

HRID 342196Notes

Reaction equation

HRID 342196 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][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]Br.[CH2:27]([NH:30][CH3:31])[CH:28]=[CH2:29]>>[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][CH2:21][CH2:22][CH2:23][CH2:24][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.[CH2:27]([N:30]([CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][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)[CH3:31])[CH:28]=[CH2:29]

Participants

6

Reactant 3

HCID 123681,6-DibromohexaneHCID 69391N-MethylallylamineHCID 154226413-(4-Bromophenyl)-6-methoxybenzo[b]thiophene

Product 3

HCID 10917490Allyl-[6-[3-(4-bromo-phenyl)-benzo[b]thiophen-6-yloxy]-hexyl]methyl-amineHCID 109726966-(6-Bromo-hexyloxy)-3-(4-bromo-phenyl)-benzo[b]thiopheneHCID 179328883-(4-Bromo-phenyl)-benzo[b]thiophen-6-ol

Procedure

From 3-(4-bromo-phenyl)-6-methoxy-benzo[b]thiophene, after cleavage of the methoxy protecting group (analogously to Ex. Ab), reaction with 1,6-dibromohexane (analogously to Ex. Ac) and N-allyl-methyl-amine and salt formation (analogously to Ex. Ad), via 3-(4-bromo-phenyl)-benzo[b]thiophen-6-ol and via 6-(6-bromo-hexyloxy)-3-(4-bromo-phenyl)-benzo[b]thiophene there is obtained allyl-[6-[3-(4-bromo-phenyl)-benzo[b]thiophen-6-yloxy]-hexyl]methyl-amine.fumarate (1:1), MS: m/e 457 (M+H30 , Br).

Sources & evidence

ORD record
ord-60c0ad31f3934f50b2d4eb122f530373
Source dataset
uspto-grants-1999_01
Patent number
US05856503

Reaction notes

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