Ethyl Acetate → HCID 57891910, compound

Participants

Reaction Conditions

Reaction Steps

Elution with 10:90 ethyl acetate:heptane with a gradient to 30:70 ethyl acetate:heptane afforded 1-chloro-2-(4-fluorophenoxy)-4-methoxybenzene (112 mg, 0.44 mmol, 49%). 1-Chloro-2-(4-fluorophenoxy)-4-methoxybenzene (110 mg, 0.44 mmol) prepared above, was dissolved in DCM (5.00 mL) and stirred under argon at −78° C. Boron tribromide (1.0M in DCM, 2.20 mL) was then added and the reaction stirred at −78° C. for 1 h. The reaction was allowed to warm to ambient temperature overnight, quenched with saturated Na2CO3 (aq) and then the aqueous and organic layers were separated. The solvent was removed in vacuo and the crude product was purified by chromatography on silica gel. Elution with 2:98 ethyl acetate:heptane with a gradient to 20:80 ethyl acetate:heptane afforded 4-chloro-3-(4-fluorophenoxy)phenol (92 mg, 0.38 mmol, 87%). M.S. (ESI) (m/z): 237, 239 [M−H]−

Provenance & Evidence