4-BROMOMETHYLBIPHENYL

Pale yellow to beige powder

Carbon tetrabromide (8.99 g, 27.1 MMOL) and triphenyl phosphine (7.11 g, 27.1 MMOL) were added to a stirred solution of biphenyl-4-yl methanol (5.00 g, 27.1 MMOL) in dichloromethane (100 mL) at room temperature. Stirring was continued at room temperature for 1.5 hours then the solvent removed by evaporation under reduced pressure. The residue was purified by column chromatography on silica gel (1: 20 diethyl ether: cyclohexane) to give the title compound (6.37g, 95percent) as a white solid.'H NMR (400 MHz: CDCI3) : 7.6 (4 H), 7.45 (4 H), 7.35 (1 H), 4.55 (2 H).Carbon tetrabromide (8.99 g, 27.1 mmol) and triphenyl phosphine (7.11 g, 27.1 mmol) wereadded to a stirred solution of biphenyl-4-yl methanol (5.00 g, 27.1 mmol) indichloromethane (100 ml_) at room temperature. Stirring was continued at room temperaturefor 1.5 hours then the solvent removed by evaporation under reduced pressure. Theresidue was purified by column chromatography on silica gel (1:20 diethyl ether:cyclohexane) to give the title compound (6.37g, 95percent) as a white solid. General procedure: To a mixture of alcohol (1 mmol) and KBr (1.5 mmol, 0.18 g) in acetonitrile (5 mL), PReference Example 50 To a dry 250 mL three-necked flask was added phenylboronic acid (2.44 g, 0.02 mol), p-bromobenzyl bromide (4.99 g, 0.02 mol), tetrakis(triphenylphosphine)palladium (0.23 g, 0.2 mmol).Add anhydrous potassium carbonate (8.28 g, 0.06 mol), and 50 mL of toluene, 30 mL of absolute ethanol, 10 mL of deionized water was further added with sodium borohydride (0.57 g, 15 mmol), and the mixture was heated to 100 ° C in an oil bath. After the reaction was confirmed by thin-plate chromatography, silica gel column chromatography was performed with ethyl acetate and n-hexane system to collect the product, 4.07. g, yield 82.4percent.General procedure: A 100 ml round bottom flask was fitted with a reflux condenser and a magnetic stirrer bar. The flask was charged with toluene (15 ml) and the appropriate amount of catalyst reagents and the internal standard (n-Decane: 2.59 mmol). The contents were thoroughly mixed and an initial sample (t

4-(Bromomethyl)biphenyl is a biphenyl derivative used in the preparation of various pharmaceutical compounds such as protein tyrosine phosphatase 1B inhibitors. 4-(Bromomethyl)biphenyl is useful as as atom transfer radical polymerization initiator.

Molecular Weight:247.13
XLogP3:4.8
Rotatable Bond Count:2
Exact Mass:246.00441
Monoisotopic Mass:246.00441
Heavy Atom Count:14
Complexity:153
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes