4-Bromo-3-(trifluoromethyl)phenol

light yellow crystalline powder

To a solution of 3-trifluoromethylphenol (7.50 ml, 62 mmol), bromine(3.47 ml, 68 mmol) was added dropwise and the mixture was stirred at rt overnight. Ith was then poured onto water and extracted with dichloromethane. The combined organic layers were washed with 4percent sodium bicarbonate solution and brine. Solvent was removed to yield a crude product that was purified by column cromathography on silica gel using mixtures of hexane/ethyl acetate as mobil phase. 5.17g of the title compound (30percent yield).LRMS: m/z 241 (M-1)To a solution of General procedure: A reaction mixture of (4-cyanophenyl)boronic acid 5 (150 mg, 1.02 mmol, 1.0 equiv.), 4-bromo-2-chloro-6-methylphenol 6s (271 mg, 1.22 mmol, 1.2 equiv.) and potassium carbonate (353 mg, 2.55 mmol, 2.5 equiv.) in PEG400/H20 (4 mL/4 mL) was stirred at room temperaturefor 15 min, and then PdCl2 (1.8 mg, 0.01 mmol, 0.01 equiv.) wasadded to it. Stirring was continued for an additional 15 h until completeconsumption of starting material as judged by TLC. Then the reactionmixture was poured into water (20 mL) and extracted with ethyl acetate(10 mL * 4). The organic layers were washed with brine, dried overanhydrous Na2SO4, filtered and condensed. The residue was then purifiedvia flash chromatography on silica gel, eluting with EtOAc/petroleumethe to 7s as white solid in 54% yield.

Molecular Weight:241.00
XLogP3:3.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Exact Mass:239.93976
Monoisotopic Mass:239.93976
Topological Polar Surface Area:20.2
Heavy Atom Count:12
Complexity:159
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes