Hydrogen Bromide → p-Xylyl bromide

Participants

Reaction Conditions

Reaction Steps

Toluene (18 g) was added to a mixture of acetic acid (25 ml) and hydrobromic acid (95 ml), followed by trioxane (6.6 g) and benzyltriethylammonium bromide (2.0 g). The mixture was then heated to 70° C. and stirred well at the same temperature for 20 hours. After cooling to room temperature, the mixture was extracted with dichloromethane and then concentrated to give oil residue. The oil residue was distilled under vacuum to give the target product, 4-bromomethyltoluene (30.0 g). Result of measurement by NMR(CDCl3, ppm) was 2.4(3H, s), 4.5(2H, s), 7.3(4H, dd).

Provenance & Evidence