Chemical Properties
Clear colorless to yellow liquid
Uses
3-Bromocumene is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs.
Synthesis Reference(s)
The Journal of Organic Chemistry, 25, p. 1691, 1960
DOI: 10.1021/jo01080a001
Synthesis
2-Bromo-4-isopropylaniline (2.65 g, 12.4 mmol, 1.0 eq.) was added to a mixed solution consisting of 96% ethanol (23 mL) and concentrated sulfuric acid (2.5 mL) over 15 min. The reaction system was cooled to -5 °C under vigorous stirring and an aqueous solution of sodium nitrite (1.42 g, 20.7 mmol, 1.67 eq.) was added dropwise over 1 h (3 mL). After the dropwise addition, stirring was continued at -5 °C for 30 min. Subsequently, copper powder (12.0 g) was added and the reaction mixture was refluxed for 4 hours. After the reaction was completed, the reaction mixture was filtered through a glass sand core funnel. The filtrate was poured into cold water (60 mL) and the organic product was extracted with dichloromethane (4 x 50 mL). The organic extracts were combined, dried with anhydrous potassium carbonate and concentrated under reduced pressure. The residue was purified by fractional distillation under reduced pressure (11 mmHg, 89-90 °C) to give 3-isopropylbromobenzene (1.91 g, 77% yield) as a yellow oil.
References
[1] Synthesis (Germany), 2016, vol. 48, # 19, p. 3301 - 3308
[2] Journal of the Chemical Society, 1939, p. 1299,1301
[3] Journal of Organic Chemistry, 1939, vol. 4, p. 20,26
[4] Angewandte Chemie - International Edition, 2012, vol. 51, # 3, p. 794 - 797
