4-(Bromomethyl)-2-chloro-1-methoxybenzene

3-Chloro-4-methoxytoluene 8 (2.6 mL, 19.2 mmol) was dissolved in dichlomethane (30 mL) and N-bromosuccinimide (3.75 g, 21.1 mmol) was added followed by AIBN (36.0 mg). Preparation 594-(Bromomethyl)-2-chloro-1 -methoxybenzeneTo a solution of 2-chloro-1 -methoxy-4-methylbenzene (300 mg, 1 .92 mmol) in carbon tetrachloride (1 0.0 ml_) was added N-bromosuccinimide (445 mg, 2.50 mmol) and benzoylperoxide (4.6 mg, 0.0192 mmol) and the reaction heated to reflux for 4.5 hours. The reaction mixture was allowed to cool to room temperature, diluted with DCM (20.0 ml_) and partitioned with a saturated aqueous solution of sodium hydrogen peroxide (30.0 ml_). The organic layer was separated and the aqueous extracted with DCM (30 ml_). The combined organics were washed with brine (50.0 ml_), filtered through a phase separator cartridge and the solvent removed in vacuo to yield a yellow oil, which was purified by silica gel chromatography eluting with 50 percent heptane in DCM to yield the title compound (263 mg, 58percent).

Molecular Weight:235.50
XLogP3:2.9
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:233.94471
Monoisotopic Mass:233.94471
Topological Polar Surface Area:9.2
Heavy Atom Count:11
Complexity:121
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes