Bromine → o-Cresol, 4-bromo-alpha,alpha,alpha-trifluoro-

Temperature

0 °C

A round-bottom flask with stirbar was charged with 2-(trifluoromethyl)phenol (1.7 g, 10.49 mmol) in 10 mL CH2Cl2 was cooled to 0° C. Bromine (0.540 ml, 10.49 mmol) in 2 mL CH2Cl2 was added dropwise. The reaction mixture was stirred at 0° C. for 1 hour, then allowed to warm to ambient temperature over 1 hour. Aqueous NaHSO3 solution was added, and the mixture extracted with CH2Cl2. The organic phase was washed with aqueous NaHCO3 and brine, dried (MgSO4), filtered, and concentrated. The residues were purified by flash chromatography eluting with 100% CH2Cl2, to afford the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ ppm 10.90 (s, 1H), 7.63 (m, 1H), 6.98 (d, 1H).

1. temperatureto warm to ambient temperature over 1 hour
2. extractionthe mixture extracted with CH2Cl2
3. washThe organic phase was washed with aqueous NaHCO3 and brine
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residues were purified by flash chromatography
8. washeluting with 100% CH2Cl2

ORD record

ord-90fb1e4152cc41e2a18f93eb72cac321

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354422B2