Bromine → 5-Bromo-1-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}-6-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

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Reaction Steps

Bromine (16.5 mL, 0.32 mmol) was added to 1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methylpyrimidine-2,4(1H,3H)-dione 1c (48.5 g, 0.16 mol) in 145 mL of acetic acid. The resulting mixture became clear then formed precipitate within an hour. After 2 hours stirring, the yellow solid was filtered and washed with cold EtOAc to an almost white solid. The filtrate was washed with sat. NaHCO3 and dried over Na2SO4. Evaporation gave a yellow solid which was washed with EtOAC to give a light yellow solid. The two solids were combined to give 59.4 g of 1d (0.156 mol) total. 1H NMR (CDCl3) δ 2.4 (s, 3H), 5.48 (s, 2H), 7.25–7.58 (m, 3H), 8.61 (s, 1H); MS (CI) m/z 380.9 (MH+).

Provenance & Evidence