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3-(3-METHOXY-PHENYL)-THIOPHENE synthesis

4synthesis methods
-

Yield:92575-93-4 66%

Reaction Conditions:

with tetrakis(triphenylphosphine) palladium(0);potassium carbonate in 1,4-dioxane;water at 100; for 1 h;Inert atmosphere;

Steps:

18.1 Step 1) Synthesis of 3-(3-methoxyphenyl)thiophene

3-Methoxybromobenzene (5.00 g, 26.70 mol), 3-thiopheneboronic acid (5.13 g, 40.10 mmol), tetratriphenylphosphinepalladium (3.09 g, 2.67 mmol) and potassium carbonate (11.11 g, 80.38 mmol) were added into a reactionflask. 1,4-Dioxane (100 mL) and water (10 mL) were then added. The resulting mixture was heated to 100°C under theprotection of nitrogen and reacted overnight. The reaction solution was cooled to rt and filtered through a celite pad. Thefilter cake was washed with ethyl acetate (20 mL), then the filtrate was concentrated and the residue was purified bysilica gel column chromatography (PE) to give the title compound as light yellow oil (3.36g, 66%).1H NMR (400 MHz, CDCl3) δ (ppm):7.89 (dd, J = 2.7, 1.1 Hz, 1H), 7.63 (dd, J = 5.0, 2.9 Hz, 1H), 7.57 (dd, J = 5.0, 1.1Hz, 1H), 7.35 - 7.26 (m, 3H), 6.90 - 6.84 (m, 1H), 3.81 (s, 3H).

References:

EP3686201,2020,A1 Location in patent:Paragraph 0343-0344