Boron tribromide → HCID 59627687, compound

Participants

Reaction Conditions

Reaction Steps

Boron tribromide (1.068 mL, 11.30 mmol) was added dropwise to ethyl 2-(5-chloro-4-methoxy-2-methylphenyl)acetate (Intermediate 3-4; 456 mg, 1.88 mmol) in dichloromethane (10 mL) at ambient temperature under nitrogen. The resulting orange red solution was stirred at 0° C. for 45 minutes. The reaction mixture was carefully quenched with water (25 mL), extracted with EtOAc (2×100 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford crude product as a yellow gum. The crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford ethyl 2-(5-chloro-4-hydroxy-2-methylphenyl)acetate (310 mg, 72.2%) as a colourless oil which solidified on standing.

Provenance & Evidence