Benzene, 2-[[2-[(6-broMohexyl)oxy]ethoxy]Methyl]-1,3-dichloro

Uses

2-[2-(6-Bromohexyloxy)ethoxymethyl]-1,3-dichlorobenzene is an intermediate in the synthesis of Vilanterol Trifenatate-d4 (V260002). Vilanterol Trifenatate (V260000) is a long-acting β2 adrenergic receptor Agonist. It demonstrates prolonged bronchodilation in subjects with asthma and COPD.

Synthesis

100mL single-necked flask, under a nitrogen atmosphere, 2-((2,6-dichlorobenzyl)oxy)ethan-1-ol (3 g, 13.5 mmol) was dissolved in 1,6-dibromo hexane (9.7 g, 40.5 mmol) tetrabutylammonium bromide (432 mg, 1.35mmol) and 50% sodium hydroxide solution (2.5g, 62.1 mmol) was added and reacted at room temperature for 16 hours. Dichloromethane (50 mL), washed successively with water (50 mL) and saturated brine (50 mL), dried over the organic phase, filtered, concentrated and purified on a silica gel column (ethyl acetate/petroleum ether = 1/12) to give a pale yellow oil Benzene, 2-[[2-[(6-broMohexyl)oxy]ethoxy]Methyl]-1,3-dichloro.