3-Bromo-1-propanol → HCID 17352815, compound

Participants

Reaction Steps

A solution of 3-bromo-1-propanol (0.685 g, 4.93 mmol), 4-nitroguaiacol (1 g, 5.91 mmol) and tributylphosphine (1.49 g, 7.36 mmol) in 20 ml tetrahydrofuran was treated with 1,1′-(azodicarbonyl)dipiperidine (1.49 g, mmol), added portionwise over 5 mins, and the resulting mixture stirred for 16 hrs. The solvent was removed in vacuo and the residues partitioned between ethyl acetate (25 ml) and 0.5 M HCl (25 ml). The organic phase was washed with 0.5 M NaOH (4×25 ml), water (25 ml) and saturated brine (25 ml), then dried and concentrated to a pale yellow solid. This was purified by flash chromatography on silica gel (eluting with ethyl acetate-hexane) to give 1-(3-bromo-propoxy)-2-methoxy-4-nitro-benzene as a white solid (300 mg, 21%);

Provenance & Evidence