Chloromethyl Methyl Ether → HCID 21707530, compound

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 with1 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) δ6.95-7.22 (m, 4 H, ArH), 5.21 (s, 2 H, CH2), 3.52 (s, 3 H, CH3).

1. temperaturethis reaction mixture was heated
2. temperatureunder reflux for 3.5 hours (FIG. 2D)
3. temperatureThe reaction was cooled
4. custompartitioned between 1 M NaOH and ethyl ether (2×30 mL)
5. washThe organic solution was washed with1 M HCl (2×20 mL), water
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. customthe solvent removed under vacuo
9. customto afford a oily residue
10. customThe crude product was purified by column chromatography (EtOAc:hexanes; 5:95)

ORD record

ord-a8ffcd2449fb45a2a2131893d1d74edc

Source dataset

uspto-grants-2001_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06284918B1