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

Tetrahedron

Facile preparation of aromatic esters from aromatic bromides with ethyl formate or DMF and molecular iodine via aryllithium

S Ushijima, K Moriyama, H Togo

Index: Ushijima, Sousuke; Moriyama, Katsuhiko; Togo, Hideo Tetrahedron, 2012 , vol. 68, # 24 p. 4701 - 4709

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Citation Number: 12

Abstract

Various aromatic bromides were treated with n-BuLi and subsequently with ethyl formate, followed by the reaction with ethanol and molecular iodine in the presence of K2CO3 to provide the corresponding aromatic ethyl esters in good yields. Moreover, aromatic bromides could be transformed into the corresponding aromatic methyl esters in good yields by the treatment with n-BuLi and subsequently with DMF, followed by the reaction with ...

1-Propanol Structure

4-Bromoanisole Structure

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~21%

Benzoic acid,4-methoxy-, 1-methylethyl ester Structure

Benzoic acid,4-...

Detail

Methanol Structure

2-Methoxynaphthalene Structure

2-Methoxynaphthalene

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~67%

2-Naphthalenecarboxylicacid, 3-methoxy-, methyl ester Structure

2-Naphthaleneca...

Methanol Structure

1,2-Dimethoxybenzene Structure

1,2-Dimethoxybenzene

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~54%

Benzoic acid,2,3-dimethoxy-, methyl ester Structure

Benzoic acid,2,...

1,3,5-Tribromobenzene Structure

1,3,5-Tribromob...

Ethyl formate Structure

~90%

3,5-dibromobenzoic acid ethyl ester Structure

3,5-dibromobenz...

Methanol Structure

4-Bromoanisole Structure

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~8%

Methyl anisate Structure

Detail

4-Bromoanisole Structure

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~28%

p-Methoxy-N,N-dimethylbenzamide Structure

p-Methoxy-N,N-d...

4-Methoxybenzaldehyde Structure

4-Methoxybenzal...

Methanol Structure

4-Bromoanisole Structure

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~13%

Methyl anisate Structure

Detail

4-Bromoanisole Structure

Ethanol Structure

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~7%

Ethyl 4-methoxybenzoate Structure

Ethyl 4-methoxy...

Detail

Methanol Structure

4-Bromoanisole Structure

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~82%

Methyl anisate Structure

Methanol Structure

4-Bromochlorobenzene Structure

4-Bromochlorobenzene

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~14%

Methyl 4-chlorobenzoate Structure

Methyl 4-chloro...

Detail

1,3-Difluorobenzene Structure

1,3-Difluorobenzene

Ethyl formate Structure

~63%

2,6-Difluorobenzaldehyde Structure

2,6-Difluoroben...

Ethyl 2,6-difluorobenzoate Structure

Ethyl 2,6-diflu...

methylimidazole Structure

methylimidazole

Methanol Structure

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~76%

Methyl 1-methyl-1H-imidazole-2-carboxylate Structure

Methyl 1-methyl...

Detail

Methanol Structure

1,3,5-Trimethoxybenzene Structure

1,3,5-Trimethox...

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~45%

2,4,6-Trimethoxybenzaldehyde Structure

2,4,6-Trimethox...

Detail

Benzo[d]thiazole Structure

Benzo[d]thiazole

Ethyl formate Structure

~74%

Ethyl 1,3-benzothiazole-2-carboxylate Structure

Ethyl 1,3-benzo...

1,3-Dimethoxybenzene Structure

1,3-Dimethoxybenzene

Ethyl formate Structure

~49%

2,6-DIMETHOXYBENZALDEHYDE Structure

2,6-DIMETHOXYBE...

Coumarone Structure

Methanol Structure

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~62%

2-Benzofurancarboxylicacid, methyl ester Structure

2-Benzofurancar...

Methanol Structure

3-Bromotoluene Structure

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~11%

Benzamide,N,N,3-trimethyl- Structure

Benzamide,N,N,3...

Detail

2,4,6-Trimethylbromobenzene Structure

2,4,6-Trimethyl...

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~65%

N,N,2,4,6-pentamethylbenzamide Structure

N,N,2,4,6-penta...

Coumarone Structure

Ethyl formate Structure

~99%

Ethyl benzofuran-2-carboxylate Structure

Ethyl benzofura...

Thianaphthene Structure

Ethyl formate Structure

~74%

Ethyl benzo[b]thiophene-2-carboxylate Structure

Ethyl benzo[b]t...

Methanol Structure

m-Bromoanisole Structure

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~8%

Methyl 3-methoxybenzoate Structure

Methyl 3-methox...

Detail

Methanol Structure

2-Bromonaphthalene Structure

2-Bromonaphthalene

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~5%

N,N-dimethylnaphthalene-2-carboxamide Structure

N,N-dimethylnap...

Detail

Bromothiophene Structure

Methanol Structure

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~12%

2-(Carbomethoxy)thiophene Structure

2-(Carbomethoxy...

Detail

1-Iodo-3,5-bis(trifluoromethyl)benzene Structure

1-Iodo-3,5-bis(...

Ethyl formate Structure

~55%

ethyl 3,5-bis(trifluoromethyl)benzoate Structure

ethyl 3,5-bis(t...

4-Bromochlorobenzene Structure

4-Bromochlorobenzene

Ethyl formate Structure

~77%

Ethyl 4-chlorobenzoate Structure

Ethyl 4-chlorob...

1-Chloro-4-iodobenzene Structure

1-Chloro-4-iodo...

Ethyl formate Structure

~55%

Ethyl 4-chlorobenzoate Structure

Ethyl 4-chlorob...

1-Bromo-3-chlorobenzene Structure

1-Bromo-3-chlor...

Ethyl formate Structure

~76%

Ethyl 3-chlorobenzoate Structure

Ethyl 3-chlorob...

Methanol Structure

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

1,4-Dimethoxybenzene Structure

1,4-Dimethoxybenzene

~70%

methyl 2,5-dimethoxybenzoate Structure

methyl 2,5-dime...

Methanol Structure

4-Bromotoluene Structure

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~9%

methyl p-toluate Structure

methyl p-toluate

Detail

Phenylacetylene Structure

Phenylacetylene

Ethyl formate Structure

~70%

Ethyl 3-phenyl-2-propynoate Structure

Ethyl 3-phenyl-...

1,4-Diiodobenzene Structure

1,4-Diiodobenzene

Ethyl formate Structure

~67%

Iodobenzene Structure

Ethyl 4-iodobenzoate Structure

Ethyl 4-iodobenzoate

methyl formate Structure

4-Bromobenzotrifluoride Structure

4-Bromobenzotri...

~59%

Methyl 4-trifluoromethylbenzoate Structure

Methyl 4-triflu...

Methanol Structure

2-Bromotoluene Structure

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~7%

Methyl o-methylbenzoate Structure

Methyl o-methyl...

Detail

methylimidazole Structure

methylimidazole

Ethyl formate Structure

~68%

Ethyl 1-methyl-1H-imidazole-2-carboxylate Structure

Ethyl 1-methyl-...

Isopropyl formate Structure

Isopropyl formate

4-Bromobenzotrifluoride Structure

4-Bromobenzotri...

~58%

Isopropyl 4-(trifluoromethyl)benzoate Structure

Isopropyl 4-(tr...

Methanol Structure

1-Bromonaphthalene Structure

1-Bromonaphthalene

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~61%

1-Naphthalenecarboxylicacid, methyl ester Structure

1-Naphthaleneca...

Detail

2-Bromopyridine Structure

2-Bromopyridine

Ethyl formate Structure

~71%

Ethyl 2-picolinate Structure

Ethyl 2-picolinate

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