Benzyl Bromide → 1,1'-[(4-Bromo-1,3-phenylene)bis(oxymethylene)]dibenzene

Participants

Reaction Conditions

Reaction Steps

106.6 g (0.771 mol, 3 eq) of potassium carbonate (325 mesh) are added to a solution of 50.1 g (0.257 mol, 1 eq) of 4-bromoresorcinol at 97% in 500 ml of acetone. The reaction medium is cooled to 5-10° C. and 75 ml (0.630 mol, 2.45 eq) of benzyl bromide are added dropwise. The reaction medium is stirred at ambient temperature overnight and is then heated at 50° C. for 2 hours. The solvent is evaporated off and the residue is then taken up with a water/ethyl acetate mixture. The aqueous phase is extracted with ethyl acetate, and the organic phases are combined, washed with a saturated solution of sodium chloride, dried over magnesium sulphate, filtered and evaporated. The residue (114.34 g) is chromatographed on silica gel (600 g), elution being carried out with 90/10 heptane/dichloromethane. 94.4 g of 2,4-bis(benzyloxy)-1-bromobenzene are obtained in the form of white crystals. Yield=99%.

Provenance & Evidence