Benzoyl Peroxide → 2-Chloro-4-(chloromethyl)pyrimidine

Participants

Reaction Steps

The mixture of 2-Chloro-4-methyl-pyrimidine (51) (6.48 g, 50 mmol), N-chloro succinimide (8.0 g, 60 mmol), and benzoyl peroxide (2.42 g, 10 mmol) in carbon tetrachloride (100 ml) was refluxed for 22 hr. After cooling to room temperature, the mixture was filtered and the filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ether:hexane (1:2)) to afford 3.3 g (40%). 1H NMR (200 MHz, CDCl3) δ: 4.57 (2H, s), 7.50 (1H, d, J=5.2 Hz), 8.65 (1H, d, J=5.2 Hz).

Provenance & Evidence