Diethyl Ether → HCID 22450976, compound

HRID 2185598Notes

Reaction equation

HRID 2185598 reaction equation
[F:1][C:2]1[C:3]([OH:24])=[CH:4][C:5]2[CH:9]=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:12][CH:11]=3)[S:7][C:6]=2[C:22]=1[F:23].CCOCC.[CH2:30](Br)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[F:1][C:2]1[C:3]([O:24][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:4][C:5]2[CH:9]=[C:8]([C:10]3[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:14][CH:15]=3)[S:7][C:6]=2[C:22]=1[F:23]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 123691-BromoheptaneHCID 22450971HCID 22450971, compound

Product 1

HCID 22450976HCID 22450976, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

is obtained by reacting 2,3-difluoro-4-ethoxythiophenol (obtainable analogously to Reference 7 from 2,3-difluoro-4-ethoxyaniline [189751-13-1]) and 4-hexylphenacyl bromide analogously to Reference 5 to give 6,7-difluoro-2-(4-hexylphenyl)-5-ethoxybenzo[b]thiophene, ether cleavage by means of hydrobromic acid/acetic acid to give 6,7-difluoro-2-(4-hexylphenyl)-5-hydroxybenzo[b]thiophene and Williamson ether synthesis using heptyl bromide in 2-butanone in the presence of potassium carbonate.

Workup

  1. customto give

Sources & evidence

ORD record
ord-b7b10fb1f30f416c9e165ccdb5a6f1e0
Source dataset
uspto-grants-2002_06
Patent number
US06403172B1

Reaction notes

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