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

Experimental Study on the Reaction Pathway of α-Haloacetophenones with NaOMe: Examination of Bifurcation Mechanism

…, K Sasagawa, K Wakisaka, S Monjiyama…

Index: Tagawa, Kohei; Sasagawa, Keita; Wakisaka, Ken; Monjiyama, Shunsuke; Katayama, Mika; Yamataka, Hiroshi Bulletin of the Chemical Society of Japan, 2014 , vol. 87, # 1 p. 119 - 126

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Citation Number: 1

Abstract

The reaction of PhCOCH 2 Br and NaOMe in MeOH gave PhCOCH 2 OH as the major product and PhCOCH 2 OMe as the minor product. Substituent effects on the reactivity and product selectivity revealed that an electron-withdrawing substituent on the phenyl ring enhanced the overall reactivity and gave more alcohol than ether. It was indicated that the alcohol was formed via carbonyl addition-epoxidation, whereas the ether was formed by ...

Sodium Methylate Structure

Sodium Methylate

PTP inhibitor 1 Structure

PTP inhibitor 1

~30%

Ethanone,2-hydroxy-1-(4-methoxyphenyl) Structure

Ethanone,2-hydr...

2-methoxy-1-(4-methoxyphenyl)ethanone Structure

2-methoxy-1-(4-...

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Sodium Methylate Structure

Sodium Methylate

2-Chloro-1-(4-methoxyphenyl)ethanone Structure

2-Chloro-1-(4-m...

~%

Ethanone,2-hydroxy-1-(4-methoxyphenyl) Structure

Ethanone,2-hydr...

2-methoxy-1-(4-methoxyphenyl)ethanone Structure

2-methoxy-1-(4-...

Learn More

PTP inhibitor 1 Structure

PTP inhibitor 1

~%

Ethanone,2-hydroxy-1-(4-methoxyphenyl) Structure

Ethanone,2-hydr...

2-methoxy-1-(4-methoxyphenyl)ethanone Structure

2-methoxy-1-(4-...

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Ethanone, 2-chloro-1-(3-methylphenyl)- (9CI) Structure

Ethanone, 2-chl...

Sodium Methylate Structure

Sodium Methylate

~%

N/A Structure

2-hydroxy-1-(3-methylphenyl)ethanone Structure

2-hydroxy-1-(3-...

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Sodium Methylate Structure

Sodium Methylate

4-Fluorophenacyl chloride Structure

4-Fluorophenacy...

~%

4'-Fluoro-2-hydroxyacetophenone Structure

4'-Fluoro-2-hyd...

1-(4-Fluorophenyl)-2-methoxyethan-1-one Structure

1-(4-Fluorophen...

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Sodium Methylate Structure

Sodium Methylate

p-Fluorophenacyl bromide Structure

p-Fluorophenacy...

~%

4'-Fluoro-2-hydroxyacetophenone Structure

4'-Fluoro-2-hyd...

1-(4-Fluorophenyl)-2-methoxyethan-1-one Structure

1-(4-Fluorophen...

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p-Fluorophenacyl bromide Structure

p-Fluorophenacy...

~%

4'-Fluoro-2-hydroxyacetophenone Structure

4'-Fluoro-2-hyd...

1-(4-Fluorophenyl)-2-methoxyethan-1-one Structure

1-(4-Fluorophen...

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Sodium Methylate Structure

Sodium Methylate

4-Fluorophenacyl chloride Structure

4-Fluorophenacy...

~%

4'-Fluoro-2-hydroxyacetophenone Structure

4'-Fluoro-2-hyd...

1-(4-Fluorophenyl)-2-methoxyethan-1-one Structure

1-(4-Fluorophen...

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Sodium Methylate Structure

Sodium Methylate

p-Fluorophenacyl bromide Structure

p-Fluorophenacy...

~%

4'-Fluoro-2-hydroxyacetophenone Structure

4'-Fluoro-2-hyd...

1-(4-Fluorophenyl)-2-methoxyethan-1-one Structure

1-(4-Fluorophen...

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p-Fluorophenacyl bromide Structure

p-Fluorophenacy...

~%

4'-Fluoro-2-hydroxyacetophenone Structure

4'-Fluoro-2-hyd...

1-(4-Fluorophenyl)-2-methoxyethan-1-one Structure

1-(4-Fluorophen...

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Sodium Methylate Structure

Sodium Methylate

PTP inhibitor 1 Structure

PTP inhibitor 1

~71%

Ethanone,2-hydroxy-1-(4-methoxyphenyl) Structure

Ethanone,2-hydr...

2-methoxy-1-(4-methoxyphenyl)ethanone Structure

2-methoxy-1-(4-...

Learn More

Sodium Methylate Structure

Sodium Methylate

2-Chloro-1-(4-methoxyphenyl)ethanone Structure

2-Chloro-1-(4-m...

~%

Ethanone,2-hydroxy-1-(4-methoxyphenyl) Structure

Ethanone,2-hydr...

2-methoxy-1-(4-methoxyphenyl)ethanone Structure

2-methoxy-1-(4-...

Learn More

PTP inhibitor 1 Structure

PTP inhibitor 1

~%

Ethanone,2-hydroxy-1-(4-methoxyphenyl) Structure

Ethanone,2-hydr...

2-methoxy-1-(4-methoxyphenyl)ethanone Structure

2-methoxy-1-(4-...

Learn More

Sodium Methylate Structure

Sodium Methylate

Chloromethyl p-tolyl ketone Structure

Chloromethyl p-...

~%

Ethanone,2-hydroxy-1-(4-methylphenyl) Structure

Ethanone,2-hydr...

2-methoxy-1-(4-methylphenyl)ethanone Structure

2-methoxy-1-(4-...

Learn More

Sodium Methylate Structure

Sodium Methylate

2-bromo-4'-methylacetophenone Structure

2-bromo-4'-meth...

~%

Ethanone,2-hydroxy-1-(4-methylphenyl) Structure

Ethanone,2-hydr...

2-methoxy-1-(4-methylphenyl)ethanone Structure

2-methoxy-1-(4-...

Learn More

2-bromo-4'-methylacetophenone Structure

2-bromo-4'-meth...

~%

Ethanone,2-hydroxy-1-(4-methylphenyl) Structure

Ethanone,2-hydr...

2-methoxy-1-(4-methylphenyl)ethanone Structure

2-methoxy-1-(4-...

Learn More

2-Chloro-1-(3-chlorophenyl)ethanone Structure

2-Chloro-1-(3-c...

Sodium Methylate Structure

Sodium Methylate

~88%

1-(3-chlorophenyl)-2-hydroxyethanone Structure

1-(3-chlorophen...

3'-chloro-2-methoxyacetophenone Structure

3'-chloro-2-met...

Learn More

3-Chlorophenacyl Bromide Structure

3-Chlorophenacy...

Sodium Methylate Structure

Sodium Methylate

~93%

1-(3-chlorophenyl)-2-hydroxyethanone Structure

1-(3-chlorophen...

3'-chloro-2-methoxyacetophenone Structure

3'-chloro-2-met...

Learn More

3-Chlorophenacyl Bromide Structure

3-Chlorophenacy...

~%

1-(3-chlorophenyl)-2-hydroxyethanone Structure

1-(3-chlorophen...

3'-chloro-2-methoxyacetophenone Structure

3'-chloro-2-met...

Learn More

Sodium Methylate Structure

Sodium Methylate

2-Bromo-4'-chloroacetophenone Structure

2-Bromo-4'-chlo...

~%

Ethanone,1-(4-chlorophenyl)-2-methoxy Structure

Ethanone,1-(4-c...

4-CHLORO-2-HYDROXYACETOPHENONE Structure

4-CHLORO-2-HYDR...

Learn More

2-Bromo-4'-chloroacetophenone Structure

2-Bromo-4'-chlo...

~%

Ethanone,1-(4-chlorophenyl)-2-methoxy Structure

Ethanone,1-(4-c...

4-CHLORO-2-HYDROXYACETOPHENONE Structure

4-CHLORO-2-HYDR...

Learn More

Sodium Methylate Structure

Sodium Methylate

2,4'-dichloroacetophenone Structure

2,4'-dichloroac...

~14%

Ethanone,1-(4-chlorophenyl)-2-methoxy Structure

Ethanone,1-(4-c...

4-CHLORO-2-HYDROXYACETOPHENONE Structure

4-CHLORO-2-HYDR...

Learn More

Sodium Methylate Structure

Sodium Methylate

2-Bromo-4'-chloroacetophenone Structure

2-Bromo-4'-chlo...

~%

Ethanone,1-(4-chlorophenyl)-2-methoxy Structure

Ethanone,1-(4-c...

4-CHLORO-2-HYDROXYACETOPHENONE Structure

4-CHLORO-2-HYDR...

Learn More

2-Bromo-4'-chloroacetophenone Structure

2-Bromo-4'-chlo...

~%

Ethanone,1-(4-chlorophenyl)-2-methoxy Structure

Ethanone,1-(4-c...

4-CHLORO-2-HYDROXYACETOPHENONE Structure

4-CHLORO-2-HYDR...

Learn More

Sodium Methylate Structure

Sodium Methylate

2,4'-dichloroacetophenone Structure

2,4'-dichloroac...

~80%

Ethanone,1-(4-chlorophenyl)-2-methoxy Structure

Ethanone,1-(4-c...

4-CHLORO-2-HYDROXYACETOPHENONE Structure

4-CHLORO-2-HYDR...

Learn More

Sodium Methylate Structure

Sodium Methylate

Chloromethyl p-tolyl ketone Structure

Chloromethyl p-...

~%

Ethanone,2-hydroxy-1-(4-methylphenyl) Structure

Ethanone,2-hydr...

2-methoxy-1-(4-methylphenyl)ethanone Structure

2-methoxy-1-(4-...

Learn More

Sodium Methylate Structure

Sodium Methylate

2-bromo-4'-methylacetophenone Structure

2-bromo-4'-meth...

~%

Ethanone,2-hydroxy-1-(4-methylphenyl) Structure

Ethanone,2-hydr...

2-methoxy-1-(4-methylphenyl)ethanone Structure

2-methoxy-1-(4-...

Learn More

2-bromo-4'-methylacetophenone Structure

2-bromo-4'-meth...

~%

Ethanone,2-hydroxy-1-(4-methylphenyl) Structure

Ethanone,2-hydr...

2-methoxy-1-(4-methylphenyl)ethanone Structure

2-methoxy-1-(4-...

Learn More

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