e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Bromothiophene reactions. I. Friedel??crafts acylation

MJ Del Agua, AS Alvarez??Insúa…

Index: Agua, M. J. del; Alvarez-Insua, A. S.; Conde, S. Journal of Heterocyclic Chemistry, 1981 , vol. 18, p. 1345 - 1347

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Citation Number: 10

Abstract

Abstract Friedel-Crafts acylation of 2, 5-dibromo-and 2, 3, 5-tribromothiophenes with different acyl chlorides and anhydrous aluminium trichloride has been studied. The reaction afforded a mixture of acyl derivatives and tetrabromothiophene. The results obtained suggest a mechanism which involves the formation of bromine cations in the reaction medium. Several products obtained in this reaction are described.

2,4-Dibromothiophene Structure

2,4-Dibromothiophene

Acetyl chloride Structure

Acetyl chloride

~91%

1-(3,5-Dibromo-2-thienyl)ethanone Structure

1-(3,5-Dibromo-...

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2,3,5-Tribromothiophene Structure

2,3,5-Tribromot...

Acetyl chloride Structure

Acetyl chloride

~21%

1-(4,5-DIBROMO-2-THIENYL)-1-ETHANONE Structure

1-(4,5-DIBROMO-...

1-(3,5-Dibromo-2-thienyl)ethanone Structure

1-(3,5-Dibromo-...

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2,5-Dibromothiophene Structure

2,5-Dibromothiophene

Acetyl chloride Structure

Acetyl chloride

~35%

2-Acetyl-5-bromothiophene Structure

2-Acetyl-5-brom...

3-Acetyl-2,5-dibromothiophene Structure

3-Acetyl-2,5-di...

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2,3,5-Tribromothiophene Structure

2,3,5-Tribromot...

Acetyl chloride Structure

Acetyl chloride

~23%

1-(4,5-DIBROMO-2-THIENYL)-1-ETHANONE Structure

1-(4,5-DIBROMO-...

1-(3,5-Dibromo-2-thienyl)ethanone Structure

1-(3,5-Dibromo-...

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Bromothiophene Structure

Chloroacetyl chloride Structure

Chloroacetyl ch...

~80%

1-(5-BROMO-THIOPHEN-2-YL)-2-CHLORO-ETHANONE Structure

1-(5-BROMO-THIO...

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2,5-Dibromothiophene Structure

2,5-Dibromothiophene

Chloroacetyl chloride Structure

Chloroacetyl ch...

~33%

Tetrabromothiophene Structure

Tetrabromothiophene

2-CHLORO-1-(2,5-DIBROMOTHIEN-3-YL)ETHANONE Structure

2-CHLORO-1-(2,5...

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2,5-Dibromothiophene Structure

2,5-Dibromothiophene

Chloroacetyl chloride Structure

Chloroacetyl ch...

~38%

Tetrabromothiophene Structure

Tetrabromothiophene

2-CHLORO-1-(2,5-DIBROMOTHIEN-3-YL)ETHANONE Structure

2-CHLORO-1-(2,5...

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Bromothiophene Structure

3-Chloropropanoyl chloride Structure

3-Chloropropano...

~75%

1-(5-bromothiophen-2-yl)-3-chloropropan-1-one Structure

1-(5-bromothiop...

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2,5-Dibromothiophene Structure

2,5-Dibromothiophene

3-Chloropropanoyl chloride Structure

3-Chloropropano...

~31%

Tetrabromothiophene Structure

Tetrabromothiophene

1-(5-bromothiophen-2-yl)-3-chloropropan-1-one Structure

1-(5-bromothiop...

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2,5-Dibromothiophene Structure

2,5-Dibromothiophene

Acetyl chloride Structure

Acetyl chloride

~5%

2-Acetyl-5-bromothiophene Structure

2-Acetyl-5-brom...

3-Acetyl-2,5-dibromothiophene Structure

3-Acetyl-2,5-di...

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2,5-Dibromothiophene Structure

2,5-Dibromothiophene

Chloroacetyl chloride Structure

Chloroacetyl ch...

~7%

Tetrabromothiophene Structure

Tetrabromothiophene

2-CHLORO-1-(2,5-DIBROMOTHIEN-3-YL)ETHANONE Structure

2-CHLORO-1-(2,5...

Detail Learn More

2,5-Dibromothiophene Structure

2,5-Dibromothiophene

3-Chloropropanoyl chloride Structure

3-Chloropropano...

~11%

Tetrabromothiophene Structure

Tetrabromothiophene

1-(5-bromothiophen-2-yl)-3-chloropropan-1-one Structure

1-(5-bromothiop...

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2,5-Dibromothiophene Structure

2,5-Dibromothiophene

4-Chlorobutyryl chloride Structure

4-Chlorobutyryl...

~12%

Tetrabromothiophene Structure

Tetrabromothiophene

4-Chloro-1-(5-bromo-thien-2-yl)butan-1-one Structure

4-Chloro-1-(5-b...

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2,3,5-Tribromothiophene Structure

2,3,5-Tribromot...

Acetyl chloride Structure

Acetyl chloride

~5%

1-(4,5-DIBROMO-2-THIENYL)-1-ETHANONE Structure

1-(4,5-DIBROMO-...

1-(3,5-Dibromo-2-thienyl)ethanone Structure

1-(3,5-Dibromo-...

Detail Learn More

2,3,5-Tribromothiophene Structure

2,3,5-Tribromot...

Chloroacetyl chloride Structure

Chloroacetyl ch...

~7%

Tetrabromothiophene Structure

Tetrabromothiophene

2-chloro-1-(4,5-dibromo-thiophen-2-yl)-ethanone Structure

2-chloro-1-(4,5...

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2,3,5-Tribromothiophene Structure

2,3,5-Tribromot...

3-Chloropropanoyl chloride Structure

3-Chloropropano...

~6%

Tetrabromothiophene Structure

Tetrabromothiophene

3-chloro-1-(4,5-dibromothiophen-2-yl)propan-1-one Structure

3-chloro-1-(4,5...

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2,3,5-Tribromothiophene Structure

2,3,5-Tribromot...

4-Chlorobutyryl chloride Structure

4-Chlorobutyryl...

~6%

Tetrabromothiophene Structure

Tetrabromothiophene

4-chloro-1-(4,5-dibromothiophen-2-yl)butan-1-one Structure

4-chloro-1-(4,5...

Detail Learn More