p-Fluoronitrobenzene → HCID 59215595, compound

Participants

Reaction Conditions

Reaction Steps

To a flask equipped with a magnetic stirrer, reflux condenser, and a nitrogen inlet was added 4-n-hexylaniline (49.1 grams, 0.283 moles), 1-fluoro-4-nitrobenzene (13.3 grams. 0.094 moles) and anhydrous methyl sulfoxide (80 ml). The contents of the flask were heated at 100° C. for 4 days; cooled to room temperature; partitioned between diethyl ether (300 ml) and water (100 ml). The ether extract was washed with water (4×100 ml) followed by brine (3×50 ml). The ether extract was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to yield a brown liquid. The brown liquid was recrystalized from hexane (500 ml) to yield 15.0 grams of product as a yellow solid. 1H NMR (CDCl3) δ 8.1(d, 2H), 7.2(d, 2H), 7.15(d, 2H),6.9(d, 2H), 6.3(bs, 1H), 2.6(t, 2H), 1.6(pent, 2H), 1.2-1.4(m, 6H), 0.9(t, 3H).

Provenance & Evidence