1,2-Dibromoethane → 1,3-Dibromo-2-(2-bromoethoxy)benzene

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Reaction Steps

A mixture of 2,6-dibromophenol (10.2 g, 40 mmol), 1,2-dibromoethane (7.6 g, 40 mmol) and NaOH (1.76 g, 44 mmol) in water was heated at reflux overnight under stirring. The mixture was cooled, extracted with diethyl ether (2×100 mL), the extract washed with aqueous NaOH, brine, dried (MgSO4) and concentrated to give the product as a pale yellow oil. Yield: 10.0 g (70%). 1H NMR (400 MHz, CDCl3) δ 3.73 (t, 2H), 4.31 (t, 2H), 6.88 (t, 1H), 7.50 (d, 2H). *Previously reported in Tetrahedron Lett. 1998, 39, 2219-2222.

Provenance & Evidence