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5-cyanobenzo[b]thiophene-2-carboxylic acid synthesis

5synthesis methods
5-CYANO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER

146137-93-1
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5-cyanobenzo[b]thiophene-2-carboxylic acid

154650-76-7
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Yield: 98.7%

Reaction Conditions:

with sodium hydroxide in 1,4-dioxane;water

Steps:

114 5-Cyano-benzthiophene-2-carboxylic acid
EXAMPLE 114 5-Cyano-benzthiophene-2-carboxylic acid 5-Cyano-benzthiophene-2-carboxylic acid from Example 113 (6.8 g, 0.0314 mol) was dissolved in dioxane (250 mL), and water (500 ml). Sodium hydroxide (10 N in water, 6.6 mL) was added slowly to the above solution at room temperature for 3 hours. The reaction mixture was then neutralized with concentrated HCl and the product was extracted with ethyl acetate (3*500 mL), dried over sodium sulfate and evaporated to give the 5-cyano-benzthiophene-2-carboxylic acid (6.28 g, 98.7% yield) as a white solid. 1H NMR (CDCl3): δ13.85 (br s, 1H), 8.58 (s, 1H), 8.33 (d, 1H, J=8.5 Hz), 8.22 (s, 1H), 7.90 (d, 1H, J=8.5 Hz).

References:

Array Biopharma Inc. US6221914, 2001, B1