ChemicalBook CAS DataBase List 5-(2-chlorophenyl)thiophene-2-carboxylic acid

5-(2-chlorophenyl)thiophene-2-carboxylic acid synthesis

5synthesis methods

Product Name:5-(2-chlorophenyl)thiophene-2-carboxylic acid
CAS Number:500604-91-1
Molecular formula:C11H7ClO2S
Molecular Weight:238.69

2-Thiophenecarboxylic acid, 5-(2-chlorophenyl)-, methyl ester

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5-(2-chlorophenyl)thiophene-2-carboxylic acid

500604-91-1
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Yield:-

Reaction Conditions:

Stage #1: methyl 5-(2-chlorophenyl)thiophene-2-carboxylatewith water;sodium hydroxide in tetrahydrofuran;methanol at 80; for 2 h;
Stage #2: with hydrogenchloride in water;

Steps:

48.A 5-(2-Chlorophenyl)thiophene-2-carboxylic acid

Example 48A
5-(2-Chlorophenyl)thiophene-2-carboxylic acid
289 mg (1.14 mmol) of the compound from Example 46A were dissolved in 2 ml of THF/methanol (1:1), and 1.14 ml (2.29 mmol) of 2 M aqueous sodium hydroxide solution were added.
The reaction mixture was stirred at 80° C. for 2 h.
After cooling to RT, the solvent was removed on a rotary evaporator and the residue was taken up in 5 ml of water and washed with 5 ml of ethyl acetate.
The aqueous phase was acidified with 1 N hydrochloric acid and extracted twice with in each case 5 ml of ethyl acetate.
The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure.
This gave, in a purity of 91%, 218 mg (73% of theory) of the target compound.
LC/MS [Method 2]: R_t=2.16 min; MS [ESIpos]: m/z=239 (M+H)⁺.

References:

US2013/190330,2013,A1 Location in patent:Paragraph 0466; 0467; 0468

7311-63-9 Synthesis