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ChemicalBook CAS DataBase List 4-Bromothiophene-2-carboxaldehyde
18791-75-8

4-Bromothiophene-2-carboxaldehyde synthesis

2synthesis methods
3-Bromothiophene

872-31-1

N,N-Dimethylformamide

68-12-2

4-Bromothiophene-2-carboxaldehyde

18791-75-8

3-Bromothiophene-2-carbaldehyde

930-96-1

General procedure: a THF solution of 1 M NaHMDS (8.8 mL, 8.8 mmol) was slowly added dropwise to the substrate (6.8 mmol) at 0°C. The reaction mixture was stirred for 30 min at 0 °C, then a solution of anhydrous THF (2 mL) with electrophilic reagent (8.3 mmol) was slowly added and stirring was continued for 3 h at 0 °C. Upon completion of the reaction, the reaction was quenched with saturated NH4Cl solution (5 mL) and diluted with hexane (20 mL). The organic layer was separated and washed with 15 wt% NaCl aqueous solution (10 mL) and subsequently concentrated to give the crude product. The product was purified by fast chromatography using a silica gel column pretreated with Et3N and 0.1% Et3N/4.9% EtOAc/95% hexane as eluent.

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Yield:18791-75-8 95%

Reaction Conditions:

with aluminium trichloride;bromine in dichloromethane for 3 h;Heating;

References:

Renault, Olivier;Dallemagne, Patrick;Rault, Sylvain [Organic Preparations and Procedures International,1997,vol. 29,# 4,p. 488 - 494]

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