Sulfur Dioxide → 1-Bromo-4-(2-methylpropyl)benzene

Participants

Reaction Steps

To a mixture of 1.78 g (10 milliMoles) of N-bromosuccinimide in 20 ml of liquid sulfur dioxide at -30° C. is added 1.57 ml (10.0 mMoles) of isobutylbenzene. The mixture is stirred at -30° to -18° for 65 minutes, then worked up as above. Assay gives only 2% p-bromoisobutylbenzene and 88% recovered starting isobutylbenzene, indicating that the reaction with NBS is very slow at this temperature.

Provenance & Evidence