4-Hexylphenacyl bromide → Acetic Acid Mixture with Hydrobromic Acid

HRID 2185597Notes

Reaction equation

HRID 2185597 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][CH3:11])[CH:5]=[CH:4][C:3]=1[SH:12].FC1C(F)=C([O:22][CH2:23][CH3:24])C=CC=1N.[CH2:25]([C:31]1[CH:40]=[CH:39][C:34]([C:35](=[O:38])[CH2:36][Br:37])=[CH:33][CH:32]=1)[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>CCOCC>[F:8][C:7]1[C:6]([O:9][CH2:10][CH3:11])=[CH:5][C:4]2[CH:36]=[C:35]([C:34]3[CH:39]=[CH:40][C:31]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:32][CH:33]=3)[S:12][C:3]=2[C:2]=1[F:1].[BrH:37].[C:23]([OH:38])(=[O:22])[CH3:24]

Participants

6

Reactant 3

HCID 129252644-Hexylphenacyl bromideHCID 224509652,3-Difluoro-4-ethoxythiophenolHCID 224509784-Ethoxy-2,3-difluoroaniline

Product 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 224509696,7-Difluoro-2-(4-hexylphenyl)-5-ethoxybenzo[b]thiophene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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. customis obtained

Sources & evidence

ORD record
ord-b6c8ec72c2fd4165b5f34a916f866cd8
Source dataset
uspto-grants-2002_06
Patent number
US06403172B1

Reaction notes

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