N-bromobutanimide → 6-(2-Bromomethyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid methyl ester

Participants

Reaction Steps

A solution of 8.55 g (29.05 mMol) 6-(2-methyl-pyrimidin-4-yloxy)-naphthalene-1-carboxylic acid methyl ester, 13.5 g N-bromo-succinimide (95%; 72.6 mMol) and 3.31 g (20 mMol) α,α-azoisobytyronitrile in 1.85 l CCl4 is heated to 80° C. and irradiated (125 W lamp) for 2 days. Then 5.44 g N-bromo-succinimide and 1.66 g α,α-azoisobytyronitrile are added and irradiation at 80° C. is continued for another day. The reaction mixture is concentrated, the residue re-dissolved in EtOAc and water, the aq. layer separated off and extracted with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Column chromatography (SiO2; hexane/EtOAc 1:1) gives the title compound: MS: [M+1]+=373/375; TLC(hexane/EtOAc 1:1): Rf=0.35.

Provenance & Evidence