Ruthenium-catalyzed intramolecular selective halogenation of O-methylbenzohydroximoyl halides: a new route to halogenated aromatic nitriles

…, S Pimparkar, M Jeganmohan

Index: Chinnagolla, Ravi Kiran; Pimparkar, Sandeep; Jeganmohan, Masilamani Chemical Communications, 2013 , vol. 49, # 30 p. 3146 - 3148

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Citation Number: 16

Abstract

The intramolecular halogenation of O-methylbenzohydroximoyl halides in the presence of a Ru catalyst and the ligand diphenylacetylene afforded halo substituted aromatic nitriles in a highly regioselective manner. Further, substituted nitriles were converted into substituted tetrazole derivatives in the presence of NaN3 and I2.

 Related Synthetic Route
Methanol Structure

67-56-1

Methanol

N-HYDROXY-4-METHOXYBENZENECARBOXIMIDOYL CHLORIDE Structure

38435-51-7

N-HYDROXY-4-MET...

~86%

Methyl anisate Structure

121-98-2

Methyl anisate

N,3-dimethoxybenzimidoyl bromide Structure

1428637-18-6

N,3-dimethoxybe...

~92%

2-Bromo-5-methoxybenzonitrile Structure

138642-47-4

2-Bromo-5-metho...

3-bromo-4-methoxybenzonitrile Structure

137042-67-2

3-bromo-4-metho...

~95%

3-Bromo-4-methoxybenzonitrile Structure

117572-79-9

3-Bromo-4-metho...

4-(dimethylamino)-N-methoxybenzimidoyl bromide Structure

1428637-16-4

4-(dimethylamin...

~82%

3-bromo-4-(dimethylamino)benzonitrile Structure

348640-88-0

3-bromo-4-(dime...

N,4-dimethoxybenzimidoyl chloride Structure

137042-63-8

N,4-dimethoxybe...

~85%

3-Chloro-4-methoxybenzonitrile Structure

102151-33-7

3-Chloro-4-meth...

N/A Structure

1428637-05-1

N/A

~86%

BENZONITRILE, 3-CHLORO-4-HYDROXY-5-METHOXY- Structure

5485-88-1

BENZONITRILE, 3...

4-hydroxy-N-methoxybenzimidoyl bromide Structure

1428637-13-1

4-hydroxy-N-met...

~92%

2-bromo-4-cyanophenol Structure

2315-86-8

2-bromo-4-cyano...

4-hydroxy-N,3-dimethoxybenzimidoyl bromide Structure

1428637-17-5

4-hydroxy-N,3-d...

~88%

BENZONITRILE, 3-BROMO-4-HYDROXY-5-METHOXY- Structure

52805-45-5

BENZONITRILE, 3...

4-hydroxy-N-methoxybenzimidoyl chloride Structure

1428636-98-9

4-hydroxy-N-met...

~95%

3-chloro-4-hydroxybenzonitrile Structure

2315-81-3

3-chloro-4-hydr...

4-ethoxy-N-methoxybenzimidoyl chloride Structure

1428637-01-7

4-ethoxy-N-meth...

~91%

3-Chloro-4-ethoxybenzonitrile Structure

916596-02-6

3-Chloro-4-etho...


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