Reaktion #57521

Reaktionsgleichung

(6-bromo-3-bromomethyl-benzofuran-2-yl)-(2,4-dichlorophenyl)-methanone

2-methoxyethylamine

potassium carbonate

→

desired product

Ausbeute 48.2%

{6-Bromo-3-[(2-methoxy-ethylamino)-methyl]-benzofuran-2yl}-(2,4-dichlorophenyl)-methanone

Ausbeute 48.2%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe resulting precipitate was removed by filtration
2. 2
   Einengenthe filtrate was concentrated
3. 3
   SonstigeThe crude residue was purified by column chromatography (30-50% ethyl acetate in hexanes)

Vorschrift

To a solution of 2-methoxyethylamine (118 mg, 1.57 mmol) in THF (6 mL) at 0° C. was added potassium carbonate followed by slow addition of (6-bromo-3-bromomethyl-benzofuran-2-yl)-(2,4-dichlorophenyl)-methanone (660 mg, 1.43 mmol) in several portions. The reaction mixture was stirred at rt for 2 h, and the resulting precipitate was removed by filtration and the filtrate was concentrated. The crude residue was purified by column chromatography (30-50% ethyl acetate in hexanes) giving the desired product (315 mg, 44% yield) as a light yellow viscous oil. 1H-NMR (acetone): δ 8.05 (d, 1H), 7.78 (d, 1H), 7.66 (m, 2H), 7.56 (dd, 1H), 7.50 (dd, 1H), 4.25 (s, 2H), 3.41 (t, 2H), 3.25 (s, 3H), 2.74 (t, 2H). LC-MS RT=2.71 min; [M+H]+=456.0.

Quelle