4-Trifluoromethoxybenzyl Bromide is a useful synthetic intermediate. It is used to prepare (nitro)[(trifluoromethoxy)benzyloxy]dihydroimidazo[2,1-b][1,3]oxazines with antitubercular activities. It is also used to synthesize tetrahydronaphthalenols with anti-allergic activities.
Colorless to light yellow liqui
4-(Trifluoromethoxy)benzyl bromide may be used in the synthesis of bioreductive drug, (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824).
Polymerizations of 4-(trifluoromethoxy)benzyl bromide, via Friedel-Crafts polymerization using aluminum chloride as a catalyst has been reported.
Synthesis of 1-(bromomethyl)-4-(trifluoromethoxy)benzene: Phosphorus tribromide (6 g, 22.2 mmol) was slowly added dropwise to a solution of (4-(trifluoromethoxy)phenyl)methanol (3.6 g, 18.8 mmol) in dichloromethane (60 mL) at 0-10 °C and stirred for 30 min. The reaction mixture was then continued to stir at room temperature for 3 hours. Upon completion of the reaction, the reaction was terminated by the addition of water (30 mL) and the mixture was washed sequentially with aqueous sodium bicarbonate (2 x 30 mL) and brine (30 mL). The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure to give 4-trifluoromethoxybenzyl bromide (3.5 g, 66% yield) as a yellow oil.
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