1-Bromo-3-phenylpropane

Colorless to light yellow liqui

1-Bromo-3-phenylpropane is used in the synthesis of MraY natural inhibitors as antibacterial agents. Also used in the preparation of quinolinone derivatives as potent and selective MAO-B inhibitors.

Chemical and Pharmaceutical Bulletin, 31, p. 4189, 1983 DOI: 10.1248/cpb.31.4189

Phenylpropanol (137 g, 1 mol) was dissolved in dichloromethane solvent containing triethylamine (205 g, 2 mol). 900 mL, cooled down to 0-5 C, slowly added methanesulfonyl chloride (172 g, 1.5 mol) dropwise, dropwise, slowly increased to 25-30 C, stirring . Reaction 2 ~ 4h, TLC to monitor the completion of the reaction, the reaction solution was concentrated to dryness, to obtain the compound of formula 3; without separation, add an appropriate amount of DMF Dissolve, add sodium bromide (255g, 2.5mol), stir the reaction at 25-30 for 6-8h, TLC to monitor the completion of the reaction, filtration, filter The liquid was added with 800 mL of water and 1000 mL of ethyl acetate, extracted and partitioned, the organic layer was washed, dried and concentrated to obtain about 160 g of 1-bromo-3-phenylpropane.

Wash the bromide successively with conc H2SO4, water, 10% aqueous Na2CO3 and again with water, then dry it with CaCl2 and fractionally distil it just before use. [Beilstein 5 IV 982.]