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

A novel electrophilic fluorination of activated aromatic rings using acetyl hypofluorite, suitable also for introducing fluorine-18 into benzene

O Lerman, Y Tor, D Hebel, S Rozen

Index: Lerman, Ori; Yitzhak, Tor; Hebel, David; Rozen, Shlomo Journal of Organic Chemistry, 1984 , vol. 49, p. 806 - 813

Full Text: HTML

Citation Number: 72

Abstract

Acetyl hypofluorite (1) is a new compound that serves as a novel electrophilic fluorinating agent. It is special in the sense that, while it is very reactive, it is still a milder reagent than other fluoroxy compounds such as CF30F or CF3COOF. It is synthesized directly from elemental fluorine and is used without any isolation or purification. The hypofluorite 1 reacts efficiently and selectively with activated aromatic rings, particularly phenol and aniline ...

Trifluoroacetanilide Structure

Trifluoroacetanilide

~55%

Acetanilide, 2,2,2,2-tetrafluoro- Structure

Acetanilide, 2,...

1-Methoxynapthalene Structure

1-Methoxynapthalene

~61%

2-fluoro-1-methoxynaphthalene Structure

2-fluoro-1-meth...

1-methoxy-4-fluoronaphthalene Structure

1-methoxy-4-flu...

1,3-Dimethoxybenzene Structure

1,3-Dimethoxybenzene

~0%

1-Fluoro-2,4-dimethoxybenzene Structure

1-Fluoro-2,4-di...

4,6,6-trifluoro-3-methoxycyclohexa-2,4-dien-1-one Structure

4,6,6-trifluoro...

1,5-difluoro-2,4-dimethoxybenzene Structure

1,5-difluoro-2,...

1,5-difluoro-2,4-dimethoxybenzene Structure

1,5-difluoro-2,...

~25%

4,6,6-trifluoro-3-methoxycyclohexa-2,4-dien-1-one Structure

4,6,6-trifluoro...

Acetanilide Structure

~74%

4'-fluoroacetanilide Structure

4'-fluoroacetanilide

2'-Fluoroacetanilide Structure

2'-Fluoroacetanilide

2-(trifluoromethyl)acetanilide Structure

2-(trifluoromet...

~62%

N-[2-fluoro-6-(trifluoromethyl)phenyl]acetamide Structure

N-[2-fluoro-6-(...

3'-Methylacetanilide Structure

3'-Methylacetanilide

~10%

N-(2-fluoro-3-methylphenyl)acetamide Structure

N-(2-fluoro-3-m...

N-(2-fluoro-5-methylphenyl)acetamide Structure

N-(2-fluoro-5-m...

N-(2,4-difluoro-5-methylphenyl)acetamide Structure

N-(2,4-difluoro...

Detail

3-(trifluoromethyl)acetanilide Structure

3-(trifluoromet...

~34%

N-(2-fluoro-5-(trifluoromethyl)phenyl)acetamide Structure

N-(2-fluoro-5-(...

N-[2-fluoro-3-(trifluoromethyl)phenyl]acetamide Structure

N-[2-fluoro-3-(...

nitroanisole Structure

~40%

2-Fluoro-6-nitro anisole Structure

2-Fluoro-6-nitr...

Monobromoacetanilide Structure

Monobromoacetanilide

~24%

N-(3-bromo-2-fluorophenyl)acetamide Structure

N-(3-bromo-2-fl...

N-(5-Bromo-2-fluorophenyl)acetamide Structure

N-(5-Bromo-2-fl...

N-(3,5-dimethylphenyl)acetamide Structure

N-(3,5-dimethyl...

~67%

N-(2-fluoro-3,5-dimethylphenyl)acetamide Structure

N-(2-fluoro-3,5...

Monobromoacetanilide Structure

Monobromoacetanilide

~47%

N-(3-bromo-2-fluorophenyl)acetamide Structure

N-(3-bromo-2-fl...

N-(5-Bromo-2-fluorophenyl)acetamide Structure

N-(5-Bromo-2-fl...

3'-Methylacetanilide Structure

3'-Methylacetanilide

~10%

N-(2-fluoro-3-methylphenyl)acetamide Structure

N-(2-fluoro-3-m...

N-(2-fluoro-5-methylphenyl)acetamide Structure

N-(2-fluoro-5-m...

N-(2,4-difluoro-5-methylphenyl)acetamide Structure

N-(2,4-difluoro...

Detail

4-(trifluoromethyl)acetanilide Structure

4-(trifluoromet...

~71%

N-(2-fluoro-4-(trifluoromethyl)phenyl)acetamide Structure

N-(2-fluoro-4-(...

1,3-Dimethoxybenzene Structure

1,3-Dimethoxybenzene

~55%

1-Fluoro-2,4-dimethoxybenzene Structure

1-Fluoro-2,4-di...

4,6,6-trifluoro-3-methoxycyclohexa-2,4-dien-1-one Structure

4,6,6-trifluoro...

1,5-difluoro-2,4-dimethoxybenzene Structure

1,5-difluoro-2,...

6-Methoxyquinoline Structure

6-Methoxyquinoline

~73%

5-Fluoro-6-methoxyquinoline Structure

5-Fluoro-6-meth...

Pivalanilide Structure

~50%

N-(2,2-DIMETHYLPROPANOYL)-2-FLUOROANILINE Structure

N-(2,2-DIMETHYL...

3'-Methylacetanilide Structure

3'-Methylacetanilide

~28%

N-(2-fluoro-3-methylphenyl)acetamide Structure

N-(2-fluoro-3-m...

N-(2-fluoro-5-methylphenyl)acetamide Structure

N-(2-fluoro-5-m...

N-(2,4-difluoro-5-methylphenyl)acetamide Structure

N-(2,4-difluoro...

Detail

Triphenylamine Structure

~28%

2-fluoro-N,N-bis(2-fluorophenyl)aniline Structure

2-fluoro-N,N-bi...

2,4-difluoro-N,N-bis(2-fluorophenyl)aniline Structure

2,4-difluoro-N,...

Triphenylamine Structure

~11%

2-fluoro-N,N-bis(2-fluorophenyl)aniline Structure

2-fluoro-N,N-bi...

2,4-difluoro-N,N-bis(2-fluorophenyl)aniline Structure

2,4-difluoro-N,...

acetyl hypofluorite Structure

acetyl hypofluorite

Anisole Structure

~7%

4-Fluorobenzyl alcohol Structure

4-Fluorobenzyl ...

2-Fluoroanisole Structure

2-Fluoroanisole

4'-Methylacetanilide Structure

4'-Methylacetanilide

~84%

N-(2-fluoro-4-methylphenyl)acetamide Structure

N-(2-fluoro-4-m...