Water → HCID 17980961, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 7.61 g (0.03 mol) of 3-Bromo-6-methoxy-2-methylbenzo[b]thiophene (compound obtained in Step 2 of the synthesis of the compound 9) in 120 mL of anhydrous THF is added dropwise 11.90 mL (0.034 mol) of a 2.5M solution of nBuLi in hexane at −78° C. under nitrogen atmosphere. The resulting mixture is stirred for 30 min at −78° C., then 20 g (0.09 mol) of perfluorocyclopentene is added in a single portion. After the addition is completed, the mixture is allowed to return to room temperature, then hydrolysed with 120 mL of water. The mixture THF-water is extracted three times with 150 mL of Et2O. The resulting organic phase is washed several times with saturated aqueous NaCl solution, dried over magnesium sulfate and then concentrated under reduced pressure. The crude product purified by column chromatography on silica gel and eluted with mixtures consisting of pentane and CH2Cl2 of increasing polarity (100:0 to 80:20) gives an oily product (8.12 g, 72% yield), pure enough to be used in the next step without further purification.

Provenance & Evidence