4-Iodophenol → 4-(Thiophen-3-yl)phenol

To a 25 mL press resistant vial which contained a suspension of 4-iodo-phenol (220 mg, 1 mmol), thiophene-3-boronic acid (128 mg, 1 mmol), palladium(II) acetate (20 mg, 0.1 mmol) and triphenyl phosphine (60 mg, 0.25 mmol) in DME (10 mL) was added potassium carbonate (400 mg, 2.5 mmol), ethanol (0.25 mL) and water (0.25 mL) at rt. The tube was sealed and the mixture was allowed to stir at rt for 30 min and then was heated to 98° C. and stirred at 98° C. for 16 h. After cooling to rt, the mixture was poured onto 200 mL ice-water solution and then extracted with EtOAc (3×30 mL). The combined organic layers were washed with water (2×30 mL) and brine (20 mL). and dried over anhy. Na2SO4. The solvent was removed in vacuo to obtain the crude product which was purified by silica gel flash chromatography to afford the title product (130 mg, 70%); 1H NMR (400 MHz, CDCl3); 4.70 (s, 1H), 6.65 (d, J=6.8 Hz, 2H), 7.31-7.3 (m, 3H), 7.48 (d, J=6.8 Hz, 2H).

1. customThe tube was sealed
2. temperaturewas heated to 98° C.
3. stirringstirred at 98° C. for 16 h
4. temperatureAfter cooling to rt
5. extractionextracted with EtOAc (3×30 mL)
6. washThe combined organic layers were washed with water (2×30 mL) and brine (20 mL)
7. customand dried over anhy
8. customThe solvent was removed in vacuo
9. customto obtain the crude product which
10. customwas purified by silica gel flash chromatography

ORD record

ord-4237d59a7c3047a1ad57051cd6b25b55

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598359B2