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ChemicalBook CAS DataBase List 1-(BROMOMETHYL)-3-NITRO-5-(TRIFLUOROMETHYL)BENZENE

1-(BROMOMETHYL)-3-NITRO-5-(TRIFLUOROMETHYL)BENZENE synthesis

2synthesis methods
[3-NITRO-5-(TRIFLUOROMETHYL)PHENYL]METHANOL

180146-66-1
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1-(BROMOMETHYL)-3-NITRO-5-(TRIFLUOROMETHYL)BENZENE

180146-67-2
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Yield:180146-67-2 91%

Reaction Conditions:

with N-Bromosuccinimide;triphenylphosphine in tetrahydrofuran at 0 - 20; for 16 h;

Steps:



1-(Bromomethyl)-3-nitro-5-(trifluoromethyl)benzene. (3-Nitro-5-(trifluoromethyl)phenyl)methanol (0.5 g, 2.26 mmol) and triphenylphosphine (1.19 g, 4.5 mmol) were combined in tetrahydrofuran (15 mL) and cooled to 0° C. N-Bromosuccinimide (0.8 g, 4.8 mmol) was introduced in portions and the reaction allowed to warm to room temperature. After 16 h, the reaction mixture was diluted with ethyl acetate, washed with concentrated sodium bicarbonate (2×), brine (2×), dried over sodium sulfate, and concentrated. Column chromatography on silica gel (10% ethyl acetate/hexanes) gave 0.58 g (91%). 1H-NMR (CDCl3, 500 MHz) δ 8.42 (s, 1H), 8.39 (s, 1H), 7.97 (s, 1H), 4.90 (s, 2H).

References:

US2007/249607,2007,A1 Location in patent:Page/Page column 64

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