Thionyl Chloride → 2-bromo-4,5,6,7-tetrahydro-N-(4-fluoro-2-hydroxyphenyl)-benzo[b]thiophene-3-carboxamide

HRID 1281833Notes

Reaction equation

HRID 1281833 reaction equation
[Br:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11]([OH:13])=O.S(Cl)(Cl)=O.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=1[OH:26]>>[Br:1][C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][CH2:10][C:4]=2[C:3]=1[C:11]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=1[OH:26])=[O:13]

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 1857632-Amino-5-fluorophenolHCID 184221372-Bromo-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid

Product 1

HCID 184222552-bromo-4,5,6,7-tetrahydro-N-(4-fluoro-2-hydroxyphenyl)-benzo[b]thiophene-3-carboxamide

Procedure

In the same manner as in Starting Material Synthesis Example 60 and using 2-bromo-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid, thionyl chloride and 2-amino-5-fluorophenol, 2-bromo-4,5,6,7-tetrahydro-N-(4-fluoro-2-hydroxyphenyl)-benzo[b]thiophene-3-carboxamide is obtained.

Workup

  1. customMaterial Synthesis Example 60

Sources & evidence

ORD record
ord-ea3ca28e6dde43199a744ef4aa2a4e07
Source dataset
uspto-grants-2002_09
Patent number
US06455521B1

Reaction notes

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