![](/CAS/GIF/78071-30-4.gif)
4-METHYLTHIOPHENE-3-CARBOXYLIC ACID synthesis
- Product Name:4-METHYLTHIOPHENE-3-CARBOXYLIC ACID
- CAS Number:78071-30-4
- Molecular formula:C6H6O2S
- Molecular Weight:142.18
![3-BROMO-4-METHYLTHIOPHENE](/CAS/GIF/30318-99-1.gif)
30318-99-1
213 suppliers
$6.00/1g
![Carbon dioxide](/CAS/GIF/124-38-9.gif)
124-38-9
122 suppliers
$175.00/23402
![4-METHYLTHIOPHENE-3-CARBOXYLIC ACID](/CAS/GIF/78071-30-4.gif)
78071-30-4
103 suppliers
$34.00/100mg
Yield: 70%
Reaction Conditions:
Stage #1:3-bromo-4-methylthiophene with n-butyllithium in tetrahydrofuran;hexane at -78; for 0.5 h;
Stage #2:carbon dioxide in tetrahydrofuran;hexane at -78; for 0.5 h;
Steps:
A56.1 Step 1 : 4-methylthiophene-3-carboxylic acid (A56-1)
To a stirred solution of 3-bromo-4-methylthiophene (2.7 g, 15.6 mmol) in THF (35 mL) was added n-BuLi (1.6 M in hexane, 14.6 mL, 23.3 mmol) at -78 °C dropwise over a period of 15 min and the mixture was stirred at -78 °C for 30 min. The C02 (gaseous) was passed through the reaction mixture for 10 min and the mixture was stirred at the same temperature for 20 min. Thereafter, the reaction mixture was warmed to 0 °C, quenched with aqueous 1 M NaOH (60 mL) and washed with EtOAc (2 x 50 mL). The aqueous layer was acidified to pH ~ 5 and extracted with DCM (2 x 50 mL). The combined organic layers were washed with water (100 mL), brine (100 mL), dried over anhydrous Na2S04 and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 8% MeOH/DCM as eluent) to provide compound A56-1 (1.5 g^ 70%) as a white solid
References:
TEIJIN PHARMA LIMITED;AMGEN INC.;BECK, Hilary Plake;BOOKER, Shon Keith;BREGMAN, Howard;CEE, Victor J.;CHAKKA, Nagasree;CUSHING, Timothy D.;EPSTEIN, Oleg;FOX, Brian M.;GEUNS-MEYER, Stephanie;HAO, Xiaolin;HIBIYA, Kenta;HIRATA, Jun;HUA, Zihao;HUMAN, Jason;KAKUDA, Shinji;LOPEZ, Patricia;NAKAJIMA, Ryota;OKADA, Kazuhisa;OLSON, Steven H.;OONO, Hiroyuki;PENNINGTON, Lewis D.;SASAKI, Kosuke;SHIMADA, Keiko;SHIN, Youngsook;WHITE, Ryan D.;WURZ, Ryan P.;YI, Shuyan;ZHENG, Xiao Mei WO2015/129926, 2015, A1 Location in patent:Page/Page column 78
![4-Methylthiophene-3-carbonitrile](/CAS/GIF/73229-39-7.gif)
73229-39-7
46 suppliers
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![4-METHYLTHIOPHENE-3-CARBOXYLIC ACID](/CAS/GIF/78071-30-4.gif)
78071-30-4
103 suppliers
$34.00/100mg
![ETHYL 2-AMINO-4-METHYLTHIOPHENE-3-CARBOXYLATE](/CAS/GIF/43088-42-2.gif)
43088-42-2
166 suppliers
$5.00/250mg
![4-METHYLTHIOPHENE-3-CARBOXYLIC ACID](/CAS/GIF/78071-30-4.gif)
78071-30-4
103 suppliers
$34.00/100mg
![3-Iodo-4-methylthiophene](/CAS/GIF/16494-41-0.gif)
16494-41-0
4 suppliers
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![4-METHYLTHIOPHENE-3-CARBOXYLIC ACID](/CAS/GIF/78071-30-4.gif)
78071-30-4
103 suppliers
$34.00/100mg