2-Fluoroethanol → 1-Bromo-3-(2-fluoroethoxymethyl)benzene

A mixture of sodium hydride [60% in oil] (343, mg, 8.6 mmol) and THF at −5° C. was treated via a syringe with a solution of 2-fluoroethanol in THF over a 1 min. period, stirred for 2 min., warmed to room temperature, stirred for 15 min. at room temperature, treated with 3-bromobenzylbromide (2.5 g, 11.7 mmol), stirred for 1 h, poured into saturated ammonium chloride and extracted with ether. The extracts were combined, washed sequentially with water and brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, 20:1 hexane/ ethyl acetate as eluent, to afford 1-bromo-3-(2-fluoroethoxymethyl)benzene as a yellow oil, 1 g (58% yield), 1H NMR (DMSO-d6) δ 3.6 (dxt, 2H); 4.5 (dxt, 2H); 4.4 (s, 2 H); 7.3 (m, 2H); 7.5 (m, 2H); MS [(+)ESI] m/z 219 [M−H]+.

1. stirringstirred for 15 min. at room temperature
2. stirringstirred for 1 h
3. extractionextracted with ether
4. washwashed sequentially with water and brine
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by flash chromatography on silica gel, 20:1 hexane/ ethyl acetate as eluent

ORD-Eintrag

ord-158d176688544e6aa2e5b276473b5061

Quelldatensatz

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07423158B2