4-Isopropylnitrobenzene → 2-Bromo-4-nitro-1-(propan-2-yl)benzene

Participants

Reaction Steps

A solution of p-nitrocumene (X) (50 g, 0.300 mol, GC purity: 99.1%) and iron(III) chloride was heated to 40° C. and bromine (59.92 g, 0.375 mol) was added dropwise over a period of 3 hours. The reaction mixture was poured into 120 ml of water, sodium hydrogensulphite (40% strength in water, 20.81 g, 0.078 mol) was added dropwise and the mixture was extracted with 100 ml of chlorobenzene. After phase separation, the chlorobenzene phase was washed with 100 ml of 5% strength aqueous HCl. Removal of the chlorobenzene under reduced pressure gave 2-bromo-1-isopropyl-4-nitrobenzene (74.05 g, 96.9 GC-% by area, 98% of theory) as a yellow oil.

Provenance & Evidence