ChemicalBook CAS DataBase List 3-IODOTHIOPHENE-2-CARBOXYLIC ACID

3-IODOTHIOPHENE-2-CARBOXYLIC ACID synthesis

8synthesis methods

Product Name:3-IODOTHIOPHENE-2-CARBOXYLIC ACID
CAS Number:60166-84-9
Molecular formula:C5H3IO2S
Molecular Weight:254.05

527-72-0 Synthesis

527-72-0
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$5.00/10g

60166-84-9
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$144.00/5g

Yield:60166-84-9 95%

Reaction Conditions:

Stage #1: 2-Thiophenecarboxylic acidwith n-butyllithium in tetrahydrofuran at -78; for 0.5 h;
Stage #2: with iodine in tetrahydrofuran at -78 - 20;
Stage #3: with hydrogenchloride in water;

Steps:

1

EXAMPLE 1 Preparation of 2- (3-LODOTHIEN-2-VL) CARBOXVLIC acid A solution of 2-thiophenecarboxylic acid (12.8 g, 0.1 mol) in THF AT-78°C is treated dropwise with n-butyl lithium (88 mL of 2.5 M solution in THF, 2.2 equiv), stirred for 0.5 h, treated dropwise with a solution of iodine (28 g) in THF (1.1 equiv. ), allowed to warm to room temperature while stirring, and CONCENTRATED IN VACUO. The resultant residue is dissolved in EtOAc and extracted with 10% aqueous NA2C03. The aqueous extracts are combined, acidified with conc. HCI and extracted with EtOAc. The EtOAc extracts are combined, dried over MGS04 and concentrated in vacuo to afford the title product as a yellow-orange solid, 23.5 g (95% yield), identified by HPLC and mass spectral analyses.

References:

WO2005/12311,2005,A1 Location in patent:Page/Page column 22

62353-77-9 Synthesis