Preparation method of asymmetric structure 5-alkoxy-2,3'-bithiophene and brominated derivatives
An asymmetric structure, alkoxy technology, applied in organic chemistry and other directions, can solve the problem of high price, and achieve the effect of high yield, good selectivity and novel structure
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Embodiment 1
[0033] The preparation of asymmetric structure 5-methoxy-2,3'-bithiophene, the steps are as follows:
[0034] (1) Preparation of 5-methoxy-2,3′-bithiophene
[0035] 2-Bromo-5-methoxythiophene, (0.3573 g, 1.85 mmol), 3-thiopheneboronic acid (0.2845 g, 2.22 mmol, 1.2 eq ), anhydrous potassium carbonate (0.6395 g, 4.63 mmol, 2.5 eq), tetrakistriphenylphosphine palladium (0.1069 g, 0.09 mmol, 0.05 eq), after vacuuming and replacing argon three times, add 5mL tetrahydrofuran to the system, 2 mL water (deoxidized) in the oil The temperature was slowly raised to 85 °C in the bath, and the reaction was refluxed for 9 h under stirring. Cool down to room temperature, spot the plate, there is no raw material 2-bromo-5-methoxythiophene, transfer the reaction solution into a separatory funnel, extract with dichloromethane, combine the organic phases, wash with water, add anhydrous MgSO 4Dry, filter, and concentrate to give the crude product. The crude product was subjected to column chr...
Embodiment 2
[0047] The preparation of asymmetric structure 5-(3-bromopropyl)-2,3'-bithiophene, the steps are as follows:
[0048] (1) Preparation of 5-(3-bromopropoxy)-2,3′-bithiophene
[0049] In 50 mL Schlenk, add 2-bromo-5-(3-bromopropoxy)-thiophene, (0.1780 g, 0.59 mmol), 3-thiopheneboronic acid (0.0906 g, 0.71 mmol, 1.2 eq ), anhydrous carbonic acid Potassium (0.2039 g, 1.48mmol, 2.5 eq), tetrakistriphenylphosphine palladium (34.1 mg, 0.03 mmol, 0.05 eq), after vacuuming and replacing argon three times, add 5 mL tetrahydrofuran, 2 mL water (after Oxygen removal treatment) was placed in an oil bath and slowly raised to 80 °C, and refluxed for 12 h under stirring. Cool down to room temperature, point the plate, no raw material 2-bromo-5-(3-bromopropoxy)-thiophene, transfer the reaction solution into a separatory funnel, extract with dichloromethane, combine the organic phases, wash with water, add Anhydrous MgSO 4 Dry, filter, and concentrate to give the crude product. The crude pr...
Embodiment 3
[0060] (1) Preparation of 5-propoxy-2,3′-bithiophene
[0061] In 50 mL Schlenk, add 2-bromo-5-propoxythiophene (0.2054 g, 0.93 mmol), 3-thiopheneboronic acid (0.1426 g, 1.11 mmol, 1.2 eq ), anhydrous potassium carbonate (0.3213 g, 2.33 mmol , 2.5eq), tetrakistriphenylphosphine palladium (0.0537 g, 0.05 mmol, 0.05 eq), after vacuuming and replacing argon three times, add 5 mL tetrahydrofuran to the system, 2 mL water (after deoxygenation treatment) in the oil The temperature was slowly raised to 80 °C in the bath, and the reaction was refluxed for 15 h under stirring. Cool down to room temperature, spot the plate, there is no raw material 2-bromo-5-propoxythiophene, transfer the reaction solution into a separatory funnel, extract with dichloromethane, combine the organic phases, wash with water, add anhydrous MgSO 4 Dry, filter, and concentrate to give the crude product. The crude product was subjected to column chromatography to obtain pure 5-propoxy-2,3′-bithiophene, 0.1709...
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