Methanol → HCID 69345556, compound

Participants

Reaction Conditions

Reaction Steps

According to Scheme 14 Step 1: BBr3 (4 eq, 65.6 mmol, 6.56 mL) was added to a solution of 1-(2-fluoro-4-chlorobenzyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one (16.4 mmol, 5.64 g) in CH2Cl2 at −50° C. The reaction mixture was stirred 1.5 hour at −40° C., overnight at room temperature then BBr3 (20 mL) was added at −30° C. and the reaction mixture was stirred 4 hours at room temperature. The reaction mixture was cooled down to −40° C. then MeOH (50 mL) was added dropwise and the crude mixture was stirred at room temperature. After evaporation, the crude mixture was purified by silica gel chromatography (300 g SiO2) using CH2Cl2/MeOH 95/5 to afford 1-(4-chloro-2-fluorobenzyl)-5-(4-hydroxyphenyl)pyridin-2(1H)-one (14.9 mmol, 4.80 g, 83%) as an orange solid.

Provenance & Evidence