Carbon tetrabromide → 1-hexyl-3-bromomethyl-4-methoxy-6-methyl-2(1H)-quinolinone

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Reaction Steps

A solution of 1 -hexyl-3-hydroxymethyl-4-methoxy-6-methyl-2(1H)-quinolinone (Example 12, 0.6 g) in methylene chloride (12 ml) containing carbon tetrabromide (1 g) was treated with triphenylphosphine (0.87 g) and stirred at ice bath temperature for 5mins and then at room temperature for hr. The reaction mixture was then evaporated under reduced pressure and the crude product was chromatographed on silica-gel (25 g). Elution with ether-hexane gave 1-hexyl-3-bromomethyl-4-methoxy-6-methyl-2(1H)-quinolinone as a white crystralline solid. That the expected product was obtained was confirmed by the spectral data: MS: m/e 365,367 (M+); NMR (CDCl3): δ4.12 (s, 3H, OCH3) 4.68 (s, 2H, CH2Br).

Provenance & Evidence