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 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).

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 with 1 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-4bc775163a4d47d5acdd77a573fd6aec

Source dataset

uspto-grants-1999_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05973191