Water → 6-Bromo-N,N-diethylhexanamide

Participants

Reaction Steps

A solution of 6-bromohexanoyl chloride (100 g, 468 mmol) in 350 ml of tetrahydrofuran was poured into a solution of diethylamine (1.08 moles, 79 g, 112 ml) in 800 ml of rapidly stirring water. The mixture was then extracted with 2×200 ml of CH2Cl2 and the pooled extracts were washed with 250 ml of brine. Drying over Na2SO4 and concentration under recuced pressure afforded 111.6 g (446 mmol, 100% yield) of product as a pale yellow oil: 1H NMR (Me2SO-d6, 300 MHz) δ3.5 (t, J=6.7 Hz, 2H), 3.2-3.3 (m, 4H), 2.3 (t, J=7.5 Hz, 2H), 1.8 (m, 2H), 1.3-1.6 (m, 4H), 1.1 (t, J=7.1 Hz, 3H), 0.99 (t, J=7.0 Hz, 3H).

Provenance & Evidence