Iodine → HCID 86672919, compound

To a mixture of magnesium turnings (0.61 g, 25.1 mmol), anhydrous THF (20 mL) and a small amount of iodine in a 300 mL flask, a solution of bromothiophene (9-5), (6.58 g, 23.9 mmol) in anhydrous THF (35 mL) was added slowly at 0° C. under N2. After refluxing for 1 h, the reaction mixture was transferred into a 250 mL flask at room temperature under N2. DMF (3.24 mL, 41.9 mmol) was added dropwise to the reaction mixture. After the mixture was stirred overnight at room temperature, the reaction was quenched by pouring cold HCl aq. (2 N) into the mixture. The product was extracted with CHCl3 and dried over anhydrous Mg2SO4. The crude product was further purified by column chromatography using hexane/CHCl3 (2:1) as the eluent to give (9-6) as a colourless oil (3.7 g, 69%). 1H NMR (CDCl3, 300 MHz, ppm): 10.03 (s, 1H), 7.64 (d, 1H, J=5.1 Hz), 6.98 (d, 1H, J=5.1 Hz), 2.89 (d, 2H, J=7.2 Hz), 1.56-1.64 (m, 1H), 1.27-1.37 (m, 8H), 0.86-0.91 (m, 6H).

1. temperatureAfter refluxing for 1 h
2. customthe reaction mixture was transferred into a 250 mL flask at room temperature under N2
3. customthe reaction was quenched
4. additionby pouring cold HCl aq. (2 N) into the mixture
5. extractionThe product was extracted with CHCl3
6. dry with materialdried over anhydrous Mg2SO4
7. customThe crude product was further purified by column chromatography

ORD record

ord-50b6ed4d6d6b4c048a4ec27618b533f9

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871884B2