Benzo[b]thiophene-2-carboxylic acid, 6-methoxy-, ethyl ester synthesis
- Product Name:Benzo[b]thiophene-2-carboxylic acid, 6-methoxy-, ethyl ester
- CAS Number:187753-62-4
- Molecular formula:C12H12O3S
- Molecular Weight:236.29
Yield:187753-62-4 88%
Reaction Conditions:
with potassium carbonate in N,N-dimethyl-formamide at 20; for 5 h;
Steps:
77.1.1
To an N,N-dimethylformamide (50 mL) solution of 2-fluoro-4-methoxybenzaldehyde (5.0 g, 32.5 mmol) and 2-mercapto-acetate (3.56 mL, 32.5 mmol) was added potassium carbonate (12.1 g, 87.5 mmol). This mixture was stirred at room temperature for 5 hours. The reaction mixture was distributed between ethyl acetate and water. The organic layer was separated followed by washing with water, drying over anhydrous magnesium sulfate and filtering. The filtrate was concentrated under a reduced pressure and the resulting residue was purified by silica gel chromatography (heptane:ethyl acetate = 20:1 to 10:1) and NH silica gel chromatography (heptane:ethyl acetate = 10:1) to obtain the title compound (6.72 g, 88%). 1H-NMR spectrum (CDCl3) δ (ppm): 1.41 (3H, t, J=7.2 Hz), 3.90 (3H, s), 4.39 (2H, q, J=7.2 Hz), 7.02 (1 H, dd, J=2.4 Hz, 9.0 Hz), 7.29 (1 H, d, J=2.4 Hz), 7.74 (1 H, d, J=9.0 Hz), 7.97 (1 H, s).
References:
EP1864980,2007,A1 Location in patent:Page/Page column 54
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