Ethanol → 2-Chloro-4-fluorobenzyl ethyl ether

Tetrahydrofuran (50 ml) was added to stirred sodium hydride (1.26 g, 0.053 mole) under a nitrogen atmosphere while being cooled in an ice-water bath. Absolute ethanol (5 ml) was then added dropwise and the reaction stirred until hydrogen evolution ceased. A solution of 2-chloro-4-fluorobenzyl bromide (10.62 g, 0.0475 mole ) in tetrahydrofuran (10 ml) was then added to the reaction mixture. The reaction mixture was allowed to stir at ambient temperature overnight. Ethanol and tetrahydrofuran were removed under reduced pressure. The reaction mixture was diluted with diethyl ether (200 ml), washed with water (4×75 ml), dried (magnesium sulfate) and concentrated under reduced pressure to remove solvent. The residue was distilled at low pressure yielding 5.27 g of 2-chloro-4-fluorobenzyl ethyl ether, b.p. 67°-68° C./10 mm Hg. The nmr spectrum was consistent with the proposed structure.

1. temperaturewhile being cooled in an ice-water bath
2. customEthanol and tetrahydrofuran were removed under reduced pressure
3. additionThe reaction mixture was diluted with diethyl ether (200 ml)
4. washwashed with water (4×75 ml)
5. dry with materialdried (magnesium sulfate)
6. concentrationconcentrated under reduced pressure
7. customto remove solvent
8. distillationThe residue was distilled at low pressure

ORD record

ord-9d30306aa07d4889b9eca28842172259

Source dataset

uspto-grants-1989_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04846882