Benzeneacetonitrile, 4-methoxy- → HCID 25215912, compound

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Reaction Steps

To a stirred and ice-cooled solution of 2-azido-1,5-dichloro-3-iodo-benzene (0.500 g, 1.5928 mmol) and 4-methoxyphenylacetonitrile (0.29 g, 1.9114 mmol) in absolute ethanol (6 ml), an ice-cooled solution of sodium methoxide (0.129 g, 2.3892 mmol) in absolute ethanol (4 ml) is added drop-wise and the mixture is allowed to reach room temperature spontaneously overnight. The resulting reaction mixture is evaporated and the gummy residue (0.740 g, 100% mass balance) is purified by column chromatography over silica gel (60-120 mesh) eluting with 0-15% ethyl acetate in hexane, to obtain the title compound as a brown solid (0.072 g, 10% yield). M.p. 72.5-73.6° C. LC-ESI-HRMS of [M+H]+ shows 460.9425 Da. Calc. 460.943317 Da, dev. −1.8 ppm.

Provenance & Evidence