1,5-Dibromopentane → 1-[(5-Bromopentyl)oxy]-3-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 3-nitrophenol (4.17 g, 30.0 mmol) and 1,5-dibromo-pentane (7.59 g, 33.0 mmol) in N-methylpyrolidinone (100 mL) was added potassium carbonate (6.21 g, 45.0 mmol), and the resulting mixture was stirred at 90° C. for 6 hours. The reaction mixture was quenched with water (30 mL) followed by extraction with ethyl acetate (30 mL×3). The combined organic layers were washed with brine and then concentrated under vacuum. The residue was purified by silica gel column chromatography to give 1-(5-bromo-pentyloxy)-3-nitro-benzene (5.10 g, 17.7 mmol, 59%) as a yellow liquid.

Provenance & Evidence