Chloromethyl Methyl Ether → HCID 21707530, compound

Participants

Reaction Steps

To a reaction mixture containing 2-fluorophenol (20, 2 g, 17.84 mmol) in 30 mL of dry pyridine was added powdered KOH (1 g, 17.71 mmol) and methoxymethyl chloride (1.8 g, 22.49 mmol) and this reaction mixture was heated under reflux for 3.5 hours (FIG. 2D). The reaction was cooled and partitioned between 1 M NaOH and ethyl ether (2×30 mL). The organic solution was washed with 1 M HCl (2×20 mL), water, and then dried (MgSO4), filtered, and the solvent removed under vacuo to afford a oily residue. The crude product was purified by column chromatography (EtOAc:hexanes; 5:95) to afford the desired product as a pale yellow oil in 62% yield. 1H NMR (CDCl3) δ 6.95-7.22 (m, 4H, ArH), 5.21 (s, 2H, CH2), 3.52 (s, 3 H, CH3).

Provenance & Evidence