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

Participants

Role	Name	HCID	Charge
Reactant	N-Methylallylamine	HCID 69391	—
Reactant	(1E)-1,4-dibromobut-1-ene	HCID 14316427	—
Reactant	3-(4-Bromophenyl)-6-methoxybenzo[b]thiophene	HCID 15422641	—
Product	3-(4-Bromo-phenyl)-benzo[b]thiophen-6-ol	HCID 17932888	—
Product	N-allyl-4-(3-(4-bromophenyl)benzo[b]thiophen-6-yloxy)-N-methylbut-2-en-1-aminium	HCID 44306432	—
Product	6-(4-(E)-bromo-but-2-enyloxy)-3-(4-bromo-phenyl)-benzo[b]thiophene	HCID 67764819	—

Reaction Steps

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).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05856503
Source dataset	uspto-grants-1999_01
ORD ID	ord-059ab091758d4d13bf30da96d258b7c2
Source note	uspto-grants-1999_01