N-bromobutanimide → Methyl 2-(bromomethyl)-3-(trifluoromethyl)benzoate

To a solution of 2-methyl-3-trifluoromethyl-benzoic acid methyl ester (0.95 g, 4.35 mmol) in benzene (10 mL) was added N-bromosuccinimide (0.77 g, 4.33 g) and benzoyl peroxide (0.052 g, 0.21 mmol) and the resulting mixture heated to reflux for 4 h, cooled and stirred at room temperature for 48 h. The mixture was filtered, the filter cake washed with diethyl ether and the filtrate washed with a 1 N sodium thiosulfate solution (10 mL), brine and dried over magnesium sulfate. The mixture was filtered and evaporated and the residue purified via automated flash chromatography (Analogix, SF25-80 g column, 5->10% ethyl acetate/hexane gradient) to give 2-bromomethyl-3-trifluoromethyl-benzoic acid methyl ester (1.04 g, 3.50 mmol, 81%) as an off white solid; 1H NMR (300 MHz, DMSO-d6) δ ppm 3.72-4.16 (m, 3H), 5.03 (s, 2H), 7.47-8.32 (m, 3H).

1. temperaturethe resulting mixture heated
2. temperatureto reflux for 4 h
3. temperaturecooled
4. filtrationThe mixture was filtered
5. washthe filter cake washed with diethyl ether
6. washthe filtrate washed with a 1 N sodium thiosulfate solution (10 mL), brine
7. dry with materialdried over magnesium sulfate
8. filtrationThe mixture was filtered
9. customevaporated
10. customthe residue purified

ORD-Eintrag

ord-4414de697e324183bc38ae8bd7141145

Quelldatensatz

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08470866B2