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

Tetrahedron

Copper (I) halide catalysed synthesis of alkyl aryl and alkyl heteroaryl ethers

MA Keegstra, THA Peters, L Brandsma

Index: Keegstra, Menno A.; Peters, Theo H. A.; Brandsma, Lambert Tetrahedron, 1992 , vol. 48, # 17 p. 3633 - 3652

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Citation Number: 114

Abstract

A number of alkyl aryl and alkyl heteroaryl ethers have been prepared from (hetero) aryl halides (mainly bromides) and sodium alkoxides, using copper (I) bromide as a catalyst. The influence of the main solvent, the halogen atom, reaction temperature and the presence of oxygen upon the rate and selectivity has been studied. Furthermore the decomposition of the catalyst and the reduction of the aryl halide are studied.

3-Bromothiophene Structure

3-Bromothiophene

Ethanol Structure

~%

3-ethoxythiophene Structure

3-ethoxythiophene

2-Bromopyridine Structure

2-Bromopyridine

Sodium Methylate Structure

Sodium Methylate

~78%

2-Methoxypyridine Structure

2-Methoxypyridine

2-Chloropyridine Structure

2-Chloropyridine

Sodium Methylate Structure

Sodium Methylate

~69%

2-Methoxypyridine Structure

2-Methoxypyridine

2-Bromofuran Structure

Sodium Methylate Structure

Sodium Methylate

~61%

2-METHOXYFURAN Structure

Bromobenzene Structure

Isopropanol Structure

~%

Isopropoxybenzene Structure

Isopropoxybenzene

benzene Structure

Sodium Methylate Structure

Sodium Methylate

1-Bromo-4-fluorobenzene Structure

1-Bromo-4-fluor...

~0%

4-Fluorobenzyl alcohol Structure

4-Fluorobenzyl ...

1,4-Dimethoxybenzene Structure

1,4-Dimethoxybenzene

Bromobenzene Structure

2-methoxyethanol Structure

2-methoxyethanol

~%

Benzene, (2-methoxyethoxy)- Structure

Benzene, (2-met...

Bromobenzene Structure

pentanol Structure

~%

(PENTYLOXY)BENZENE Structure

(PENTYLOXY)BENZENE

2-Bromofuran Structure

Ethanol Structure

~%

2-ethoxyfuran Structure

Bromobenzene Structure

Isopropanol Structure

~%

Isopropoxybenzene Structure

Isopropoxybenzene

2,5-Dibromothiophene Structure

2,5-Dibromothiophene

Sodium Methylate Structure

Sodium Methylate

~49%

2,5-Dimethoxythiophene Structure

2,5-Dimethoxyth...

Bromothiophene Structure

Sodium Methylate Structure

Sodium Methylate

~92%

Thiophene(SIV) Structure

2-Methoxythiophene Structure

2-Methoxythiophene

Sodium Methylate Structure

Sodium Methylate

1-Bromo-4-fluorobenzene Structure

1-Bromo-4-fluor...

~82%

4-Fluorobenzyl alcohol Structure

4-Fluorobenzyl ...

1,4-Dimethoxybenzene Structure

1,4-Dimethoxybenzene

Bromothiophene Structure

Ethanol Structure

~%

Thiophene, 2-ethoxy- Structure

Thiophene, 2-ethoxy-

1-Bromonaphthalene Structure

1-Bromonaphthalene

Sodium Methylate Structure

Sodium Methylate

~92%

1-Methoxynapthalene Structure

1-Methoxynapthalene

3-Bromopyridine Structure

3-Bromopyridine

Sodium Methylate Structure

Sodium Methylate

~41%

3-Methoxypyridine Structure

3-Methoxypyridine

Selective and efficient syntheses of phototoxic 2, 2′: 5′, 2...

[Rossi; Carpita; Ciofalo; Lippolis Tetrahedron, 1991 , vol. 47, # 39 p. 8443 - 8460]