Carbon Dioxide → HCID 11287530, compound

Participants

Reaction Conditions

Reaction Steps

At −100° C., n-BuLi (25 ml, 15% in n-hexane, 4.1 mmol) was added to a solution of 1-bromo-2-methoxy-4-methylsulfanyl-3-vinylbenzene (7 g, 31.3 mmol) in THF (300 ml), and the mixture was stirred at −100° C. for 20 min. At −100° C., CO2 was then introduced (exothermic reaction up to −60° C.). At −80 to −90° C., the mixture was then stirred for another 1 h, and NaOH (100 ml) was added dropwise at −40° C. The solution was stirred into EtOAc (400 ml), and the mixture was extracted 3× with 5% strength NaOH and acidified to pH=1 using 10% strength HCl. The H2O phase was extracted with EtOAc (300 ml), and the combined organic phases were dried over MgSO4 and concentrated.

Provenance & Evidence