Hydrochloric Acid → HCID 67467385, compound

Participants

Reaction Steps

Under an argon atmosphere 1-bromo-2-isobutoxy-3,4-dimethoxy-benzene (6.7 g, 23.2 mmol) was dissolved in dry THF (50 mL). The solution was cooled to −70° C. while n-BuLi (2.0 M in pentane, 12.8 mL, 25.5 mmol) was added over 10 min. The solution was stirred for 20 min at −70° C. after which trimethyl borate (5.2 mL, 46.4 mmol) was added over 10 min. The solution was kept at −70° C. for 15 min after which it was heated to RT over 15 min and stirred at RT for 30 min. Saturated aq. NH4Cl (200 mL) was added and the solution was adjusted to pH 1 with 4N HCl (10 mL). The mixture was extracted with EtOAc (×3). The combined organic phases were dried (Na2SO4), filtered and concentrated to afford an oil. The crude product was purified by flash chromatography using heptane:EtOAc 4:1->3:1 as the eluent to afford a crystalline compound which was recrystallised from petroleum ether:Et2O (90:10) to afford the title compound as a crystalline compound.

Provenance & Evidence