Preparation method of tetrahydro-cyclopentyl[2,1-b;3,4-b'] bi-thiophene ketone

A technology of 4-b and thiophenone, applied in the field of 4hydro-cyclopenta[2, can solve the problems of long reaction steps, harsh reaction conditions, and low yield, and achieve the effect of easy realization and mild conditions

Inactive Publication Date: 2010-09-15
XIAN MODERN CHEM RES INST
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Problems solved by technology

[0009] However, this method adopts a low-temperature lithium substitution approach, the reaction conditions are harsh, the reaction steps are longer, and the yield is lower. The total yield of 4 hydrogen-cyclopenta[2,1-b; 42%

Method used

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  • Preparation method of tetrahydro-cyclopentyl[2,1-b;3,4-b'] bi-thiophene ketone
  • Preparation method of tetrahydro-cyclopentyl[2,1-b;3,4-b'] bi-thiophene ketone
  • Preparation method of tetrahydro-cyclopentyl[2,1-b;3,4-b'] bi-thiophene ketone

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Embodiment 1

[0023] (1) Preparation of 3-methyl 2,2'-bithiophene

[0024] Add 3.54g (20mmol) 2-bromo-3-methylthiophene, 3.84g (30mmol) 2-thiophene boronic acid, 52.4mg (0.2mmol) triphenylphosphine, 100ml tetrahydrofuran, 100ml (2mol / L) into a 250ml three-necked flask Potassium carbonate solution was protected by argon, and after stirring, 65mg of palladium acetate was added, heated to 65°C and refluxed for 4h. Stop heating, lower to room temperature, extract the reaction system 3 times with 200ml toluene, combine the organic phases, wash the organic phases with saturated aqueous sodium chloride until neutral, then dry the organic phases with anhydrous magnesium sulfate, and filter the organic phases , the filtrate was concentrated, and then the concentrate was subjected to column chromatography to obtain 3.3 g of a colorless liquid, yield: 92%.

[0025] Structure Identification:

[0026] 1 H NMR (500MHz, CD 3 COCD 3 ): 2.36(m, 3H), 6.94(d, 1H), 7.11(t, 1H), 7.18(dd, 1H), 7.30(d, 2H), ...

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Abstract

The invention discloses a preparation method of tetrahydro-cyclopentyl[2,1-b;3,4-b'] bi-thiophene ketone, aiming to solve the problem of lower reaction yield. The invention comprises the following steps of: (1) carrying out a coupling reaction on 2-bromine-3-methyl thiophene and 3.84g of 2-thiophene boric acid to obtain 3-methyl2,2'-bithiophene; (2) carrying out an oxidation reaction on 3-methylbithiophene and potassium permanganate to obtain 2,2'-bithiophene3-formic acid; and (3) reacting the 3-methylbithiophene with concentrated sulfuric acid (98 percent) to obtain the tetrahydro-cyclopentyl[2,1-b;3,4-b'] bi-thiophene ketone. The invention is mainly used for preparing the tetrahydro-cyclopentyl[2,1-b;3,4-b'] bi-thiophene ketone.

Description

technical field [0001] The invention relates to a preparation method of 4 hydrogen-cyclopenta[2,1-b; 3,4-b']bithienone. Background technique [0002] Since Heeger et al. discovered that polyacetylene conducts electricity in 1977, conjugated polymers have attracted many scientists for their outstanding photoelectric properties. Due to the large π-conjugated main chain structure of this kind of material, it has one-dimensional charge transport characteristics, so it has excellent photoelectric properties, and has been applied or has potential applications in many optoelectronic device fields, such as polymer light-emitting diodes (PLEDs), organic Photovoltaic cells (OPV), thin film transistors (TFT), etc. [0003] 4H-cyclopenta[2,1-b; 3,4-b′]bisthiophene D-A-D type polymers containing dialkyl substitutions are a new class of conjugated polymers that can act as bulk heterojunction photovoltaic cells efficient donor material. For example, in 2007, Heeger et al. reported that ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04
Inventor 高潮蒋忠亮刘红利陈键杜渭松陈冬丛志远
Owner XIAN MODERN CHEM RES INST
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