3-Bromophenetole → Methanol

Participants

Reaction Steps

The title compound was prepared from 3-bromophenetole and 4-bromo-N-methoxy-N-methylbenzamide following the general method of Method 1. The crude product was re-crystallized from methanol affording 0.37 g (47% yield) of the title compound as colorless crystals: mp 68.5-70.1° C.; 1H NMR (400 MHz, CDCl3) δ 7.70-7.60 (m, 4 H), 7.38 (broad t, J=7.6 Hz, 1 H), 7.31-7.27 (m, 2 H), 7.13 (ddd, J=8.2, J=2.3, J=1.2 Hz, 1 H), 4.08 (q, J=7.0 Hz, 2 H), 1.43 (t, J=7.0 Hz, 3 H); 13C NMR (400 MHz, CDCl3) δ 195.5, 159.0, 138.4, 136.4, 131.6, 131.5, 129.3, 127.5, 122.5, 119.5, 114.9, 63.7, 14.7; MS (TSP) m/z 305 (M+1).

Provenance & Evidence