Hydrogen Bromide → 4-(Bromomethyl)-4'-pentyl-1,1'-biphenyl

Participants

Reaction Steps

A solution of 9.4 g of 4-(hydroxymethyl)-4'-pentylbiphenyl in 150 ml of methylene chloride was placed at 0° C. in a sulphonation flask under argon gasification and treated within 5 minutes with 3.4 ml of a 62% aqueous hydrogen bromide solution. The mixture was subsequently stirred at room temperature for a further 15 hours, then poured into 50 ml of 5% sodium hydrogen carbonate solution and extracted three times with 100 ml of methylene chloride each time. The organic phases were washed twice with 100 ml of water each time, dried over magnesium sulphate and concentrated. Low-pressure chromatography (0.5 bar) of the residue (10.8 g) on silica gel with 5% ethyl acetate/petroleum as the eluant gave 7.5 g (64%) of 4-(bromomethyl)-4'-pentylbiphenyl as a colourless oil.

Provenance & Evidence