2-Methylnaphthalene → 2-Bromomethylnaphthalene

Participants

Reaction Steps

A mixture of 250 g (1.75 m) of 2-methylnaphthalene and 312.5 g (1.75 m) of N-bromosuccinimide in 1125 ml of carbon tetrachloride in a 3 liter round bottom flask fitted with a stirrer and reflux condenser with a drying tube was refluxed for twenty hours. The insoluble succinimide (171 g, 1.73 moles) was filtered and washed with 250 ml of carbon tetrachloride. Concentrated in vacuo gave 395 g of an oil to which was added 800 ml of petroleum ether. Solid crystallized immediately and was filtered and washed with 500 ml of petroleum ether. The first crop was air-dried to give 298 g, m.p. 48°-65° C. (Lit. m.p. 56° ). Concentration of the filtrate led to the isolation of another 33 g, m.p. 45°-50° C. of product to give a total of 331 g (86%) of good quality crude product.

Provenance & Evidence