Bromine → HCID 59854089, compound

Participants

Reaction Conditions

Reaction Steps

A 350 ml sulfonation flask fitted with stirrer, reflux condenser and pressure equalized dropping funnel is charged with 2-chloro-1-{4-[4-(2-chloro-2-methyl-propionyl)-benzyl]-phenyl}-2-methyl-propan-1-one (113.1 g, 0.3 mol) and ortho-dichlorobenzene (150 ml). The mixture is heated to 150° C., and then a solution of bromine (49.6 g, 0.3 mol) in ortho-dichlorobenzene (50 ml) is added slowly in such a way that the bromine is reacted before the addition of the next drop of the bromine solution. When all the bromine has been added, the mixture is kept at 150° C. for another ten minutes, and then the ortho-dichlorobenzene is carefully removed on the rotavapor. The residue is recrystallized from hexanes to give the product (116.3 g, 85% of theory) as off white crystals, mp.=93° C. 1H-NMR (CDCl3, 400 MHz) δ 1.89 (s, 12 H, CH3); 6.29 (s, 1 H, CH); 7.54 (m, 4 H, H-4); 7.73 (m, 4 H, H-3). 13C-NMR (CDCl3, 100 MHz) δ 30.47 (C-8); 52.82 (C-1), 68.30 (C-7) 128.22 (C-3), 130.57 (C-4), 134.19 (C-5); 144.54 (C-2); 198.26 (C-6).

Provenance & Evidence