反应详情

温度

60 °C

A dry 100 mL 3-necked flask equipped with a nitrogen inlet, a condenser, a thermometer, and a magnetic stirrer was charged with 2.0 g of 3-tert-butyltoluene (Wiley Organics, Coshocton, Ohio 43812), 2.40 g of N-bromosuccinimide (Aldrich), and 30 mL of CCl4. The mixture was treated with 0.16 g of benzoyl peroxide (Aldrich) and heated at 60° C. under N2. Careful temperature control is important to minimize by-product formation. After 1 h at 60° C. the reaction mixture was cooled to 0° C., filtered to remove succinimide, and the filtrate was concentrated in vacuo to afford a light yellow liquid. Analysis of this material by tlc (SiO2, hexane) indicated a major new component at Rf=0.50, a minor component at Rf=0.55, and a trace of 3-tert-butyltoluene at Rf=0.75. The crude product was purified by flash chromatography on 100 g of silica gel (hexane) to afford 1.06 g (35%) of 3-tert-butylbenzyl bromide as a clear liquid.

1. customA dry 100 mL 3-necked flask equipped with a nitrogen inlet, a condenser
2. temperatureAfter 1 h at 60° C. the reaction mixture was cooled to 0° C.
3. filtrationfiltered
4. customto remove succinimide
5. concentrationthe filtrate was concentrated in vacuo
6. customto afford a light yellow liquid
7. customThe crude product was purified by flash chromatography on 100 g of silica gel (hexane)