Sodium Hydroxide → 3-Bromo-5-(trifluoromethyl)benzaldehyde

Temperature

0 °C

A solution of [3-bromo-5-(trifluoromethyl)phenyl]methanol (409 mg, 1.61 mmol) in CH2Cl2 (25 mL) was cooled to 0° C. and then Dess-Martin periodinane (1.02 g, 2.41 mmol) was added. The reaction was stirred at 0° C. for 30 minutes and then warmed to room temperature. After stirring at room temperature for thirty minutes, the reaction was poured into 1N NaOH (25 mL). The mixture was extracted with EtOAc (100 mL), and the organic extracts were washed with 1N NaOH (25 mL), then brine (25 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography with 25% EtOAc/hexanes afforded 3-bromo-5-(trifluoromethyl)benzaldehyde. Rf=0.60 (25% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) δ 10.02 (s, 1H), 8.20 (s, 1H), 8.07 (s, 1H), 8.02 (s, 1H).

1. temperaturewarmed to room temperature
2. stirringAfter stirring at room temperature for thirty minutes
3. extractionThe mixture was extracted with EtOAc (100 mL)
4. washthe organic extracts were washed with 1N NaOH (25 mL)
5. dry with materialbrine (25 mL), dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customPurification by flash chromatography with 25% EtOAc/hexanes

ORD record

ord-c8db1d8fd8d745c88b07a88109cc08e0

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08193365B2