3-Methoxythiophene synthesis
- Product Name:3-Methoxythiophene
- CAS Number:17573-92-1
- Molecular formula:C5H6OS
- Molecular Weight:114.17
872-31-1
124-41-4
17573-92-1
Example 2 Preparation of 3-methoxythiophene: 185 g of 3-bromothiophene (1.13 mol), 3.24 g of copper(I) bromide (CuBr, 2 mol%) and 14.1 g of PEG DME 250 (5 mol%) were added to the reactor. Subsequently, sodium methanol solution (30% concentration, precursor concentration 30.4) was added and the mixture was heated to 90 °C. The conversion was monitored by GC during the reaction and was >98% (reaction time totaled 10 hours). Upon completion of the reaction, the mixture was poured into 300 g of water. After filtration through decalite, the mixture was extracted twice with 120 g of methyl tertiary butyl ether (MTBE). The organic phases were combined and subjected to vacuum fractionation to afford 117.4 g of 3-methoxythiophene (1.03 mol, 91% yield) with a GC purity of >99% (% area).
Yield:17573-92-1 91%
Reaction Conditions:
polyethylene glycol dimethyl ether;copper(I) bromide in methanol at 90; for 10 h;
Steps:
2
EXAMPLE 2 Preparation of 3-methoxythiophene From 3-bromothiophene 185 g of 3-bromothiophene (1.13 mol) are introduced into a mixture of 3.24 g of copper(I) bromide (CuBr, 2 mol %), 14.1 g of PEG DME 250 (5 mol %) and 407 g of sodium methanolate solution in methanol (30% strength) (precursor concentration 30.4) and heated to 90° C. After the conversion, determined by GC, it is >98% (total of 10 h), the reaction mixture is added to 300 g of water. It is subsequently filtered through decalite, and the mixture is extracted twice with 120 g of MTBE each time. Vacuum fractionation of the combined organic phases results in 117.4 g of 3-methoxylthiophene (1.03 mol, 91%), GC purity >99% a/a.
References:
MEUDT, Andreas;Rausch, Bernhard J. US2008/71084, 2008, A1 Location in patent:Page/Page column 4
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