Pyridine → 4-Fluoro-2-methylphenyl Methoxyformate

Participants

Reaction Steps

4-Fluoro-2-methylphenol (4 mmol, 504 mg) in tetrahydrofuran (10 mL) under argon was treated at 0 ° C. with pyridine (8.8 mmol, 700 mg, 2.2 eq) then methyl chloroformate (4.4 mmol, 415 mg, 1.1 eq). The mixture was allowed to warm to room temperature and to stir for 45 min. It was then concentrated and dissolved in dichloromethane (10 mL), and pyridine (8.8 mmol, 700 mg, 2.2 q) then methyl chloroformate (4.4 mmol, 415 mg, 1.1 eq) were added again and allowed to react for 30 min. Then dioxane (3 mL) was added to help solubility, then pyridine (8.8 mmol, 700 mg, 2.2 eq) and methyl chloroformate (4.4 mmol, 415 mg, 1.1 eq) again 3 times. LC/MS actually showed evolution in conversion of start material after every add, but also that reaction stopped 5 min later. Achieved conversion was 85% (UV). The mixture was concentrated under reduced pressure, dissolved in dichloromethane, washed with 1M HCl aqueous solution then 10% Na2CO3 aqueous solution. Organics were dried on MgSO4 and concentrated under reduced pressure to give the title compound as an oil (2.5 mmol, 468 mg, 64% yield). M+H 185.08.

Provenance & Evidence