3-Fluoro-4-methoxyaniline → Acetic Acid Mixture with Hydrobromic Acid

HRID 2185596Notes

Reaction equation

HRID 2185596 reaction equation
F[C:2]1[CH:3]=[C:4]([SH:10])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[F:11]C1C=C(C=[CH:17][C:18]=1[O:19]C)N.[CH2:21]([C:27]1[CH:36]=[CH:35][C:30]([C:31](=[O:34])[CH2:32][Br:33])=[CH:29][CH:28]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>CCOCC>[F:11][C:3]1[C:4]2[S:10][C:31]([C:30]3[CH:35]=[CH:36][C:27]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:28][CH:29]=3)=[CH:32][C:5]=2[CH:6]=[C:7]([O:8][CH3:9])[CH:2]=1.[BrH:33].[C:18]([OH:19])(=[O:34])[CH3:17]

Participants

6

Reactant 3

HCID 5811103-Fluoro-4-methoxyanilineHCID 27590073-Fluoro-4-methoxythiophenolHCID 129252644-Hexylphenacyl bromide

Product 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 224509737-Fluoro-2-(4-hexylphenyl)-5-methoxybenzo[b]thiophene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

7-Fluoro-2-(4-hexylphenyl)-5-octyloxybenzo[b]thiophene is obtained by reacting 3-fluoro-4-methoxythiophenol (obtainable analogously to Reference 7 from 3-fluoro-4-methoxyaniline [366-99-4]) and 4-hexylphenacyl bromide analogously to Reference 5 to give 7-fluoro-2-(4-hexylphenyl)-5-methoxybenzo[b]thiophene, ether cleavage by means of hydrobromic acid/acetic acid to give 7-fluoro-2-(4-hexylphenyl]-5-hydroxybenzo[b]thiophene and Williamson ether synthesis using octyl bromide in 2-butanone in the presence of potassium carbonate.

Sources & evidence

ORD record
ord-4dcf3e14f975437dacc25a426cdac808
Source dataset
uspto-grants-2002_06
Patent number
US06403172B1

Reaction notes

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