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

Tetrahedron

Facile p-toluenesulfonic acid-promoted para-selective monobromination and chlorination of phenol and analogues

…, K Pla-on, S Aphimanchindakul, N Pungcharoenpong…

Index: Bovonsombat, Pakorn; Ali, Rameez; Khan, Chiraphorn; Leykajarakul, Juthamard; Pla-On, Kawin; Aphimanchindakul, Suraj; Pungcharoenpong, Natchapon; Timsuea, Nisit; Arunrat, Anchalee; Punpongjareorn, Napat Tetrahedron, 2010 , vol. 66, # 34 p. 6928 - 6935

Full Text: HTML

Citation Number: 28

Abstract

para-Regioselective bromination of phenol and analogues, promoted by p-toluenesulfonic acid, is achieved in high to excellent yields at room temperature with N-bromosuccinimide. Chlorination with N-chlorosuccinimide and catalysed by p-toluenesulfonic acid also gives para-chlorinated phenol analogues in good yields at room temperature.

3-Hydroxybenzaldehyde Structure

3-Hydroxybenzal...

~0%

2-Bromo-5-hydroxybenzaldehyde Structure

2-Bromo-5-hydro...

2,4-dibromo-5-hydroxybenzaldehyde Structure

2,4-dibromo-5-h...

4-BROMO-3-HYDROXYBENZALDEHYDE Structure

4-BROMO-3-HYDRO...

Methyl salicylate Structure

Methyl salicylate

~0%

Methyl 5-Bromosalicylate Structure

Methyl 5-Bromos...

3-Bromo-2-hydroxybenzoic acid methyl ester Structure

3-Bromo-2-hydro...

3-Hydroxybenzaldehyde Structure

3-Hydroxybenzal...

~41%

2-Chloro-5-hydroxybenzaldehyde Structure

2-Chloro-5-hydr...

4-Chloro-3-hydroxybenzaldehyde Structure

4-Chloro-3-hydr...

2-Chloro-3-hydroxybenzaldehyde Structure

2-Chloro-3-hydr...

2-Bromophenol Structure

~0%

2-Bromo-4-chlorophenol Structure

2-Bromo-4-chlor...

2-Bromo-6-chlorophenol Structure

2-Bromo-6-chlor...

3-Hydroxybenzaldehyde Structure

3-Hydroxybenzal...

~0%

2-Chloro-5-hydroxybenzaldehyde Structure

2-Chloro-5-hydr...

4-Chloro-3-hydroxybenzaldehyde Structure

4-Chloro-3-hydr...

2-Chloro-3-hydroxybenzaldehyde Structure

2-Chloro-3-hydr...

2-Bromophenol Structure

~41%

2-Bromo-4-chlorophenol Structure

2-Bromo-4-chlor...

2-Bromo-6-chlorophenol Structure

2-Bromo-6-chlor...

Guaiacol Structure

~43%

4-Chloroguaiacol Structure

4-Chloroguaiacol

2-Chloro-6-methoxyphenol Structure

2-Chloro-6-meth...

3-ACETYLPHENOL Structure

~33%

1-(2-chloro-5-hydroxyphenyl)ethanone Structure

1-(2-chloro-5-h...

1-(2-Chloro-3-hydroxyphenyl)ethan-1-one Structure

1-(2-Chloro-3-h...

ETHANONE, 1-(4-CHLORO-3-HYDROXYPHENYL)- Structure

ETHANONE, 1-(4-...

3-Hydroxybenzaldehyde Structure

3-Hydroxybenzal...

~0%

2-Chloro-5-hydroxybenzaldehyde Structure

2-Chloro-5-hydr...

4-Chloro-3-hydroxybenzaldehyde Structure

4-Chloro-3-hydr...

2-Chloro-3-hydroxybenzaldehyde Structure

2-Chloro-3-hydr...

Methyl salicylate Structure

Methyl salicylate

~57%

Methyl 5-chloro-2-hydroxybenzoate Structure

Methyl 5-chloro...

3-ACETYLPHENOL Structure

~46%

N/A Structure

1-(2-Bromo-5-hydroxyphenyl)ethanone Structure

1-(2-Bromo-5-hy...

1-(4-bromo-3-hydroxyphenyl)ethanone Structure

1-(4-bromo-3-hy...

3-ACETYLPHENOL Structure

~%

1-(2,4,6-Tribromo-3-hydroxyphenyl)ethan-1-one Structure

1-(2,4,6-Tribro...

1-(2-Bromo-5-hydroxyphenyl)ethanone Structure

1-(2-Bromo-5-hy...

3-ACETYLPHENOL Structure

~%

1-(2,4,6-Tribromo-3-hydroxyphenyl)ethan-1-one Structure

1-(2,4,6-Tribro...

1-(2-Bromo-5-hydroxyphenyl)ethanone Structure

1-(2-Bromo-5-hy...

1-(4-bromo-3-hydroxyphenyl)ethanone Structure

1-(4-bromo-3-hy...

Guaiacol Structure

~0%

4-Chloroguaiacol Structure

4-Chloroguaiacol

2-Chloro-6-methoxyphenol Structure

2-Chloro-6-meth...

3-Hydroxybenzaldehyde Structure

3-Hydroxybenzal...

~0%

2-Bromo-5-hydroxybenzaldehyde Structure

2-Bromo-5-hydro...

2,4-dibromo-5-hydroxybenzaldehyde Structure

2,4-dibromo-5-h...

4-BROMO-3-HYDROXYBENZALDEHYDE Structure

4-BROMO-3-HYDRO...

3-Hydroxybenzaldehyde Structure

3-Hydroxybenzal...

~%

2-Bromo-5-hydroxybenzaldehyde Structure

2-Bromo-5-hydro...

2,4-dibromo-5-hydroxybenzaldehyde Structure

2,4-dibromo-5-h...

Mild, Efficient, and Regioselective Monobromination of Aryla...

[Borikar, Sanjay P.; Daniel, Thomas; Paul, Vincent Synthetic Communications, 2010 , vol. 40, # 5 p. 647 - 653]