N,N-Diethylaniline → 3-Bromo-2-(prop-2-en-1-yl)phenol

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(allyloxy)-3-bromobenzene (3.53 g, 16.6 mmol) and Et2NPh (7.4 mL) was heated in a 220° C. oil bath. After 5 hr, the reaction mixture was cooled to room temperature, diluted with EtOAc (80 mL), and washed with 2N aq HCl (3×20 mL), water (2×20 mL), brine (10 mL), dried over Na2SO4, filtered, and concentrated in vacuo. Flash chromatography (0%-1 0% EtOAc/hexanes) gave 1.64 g (47%) of the title compound as the late eluting component, and 1.19 g (34%) of 2-allyl-5-bromophenol. 1HNMR (300 MHz, CDCl3) δ 7.17 (dd, J=8.0, 1.1, 1H), 6.97 (t, J=8.0, 1H), 6.77 (dd, J=8.0, 1.0, 1H), 6.04-5.90 (m, 1H), 5.15 (t, J=1.7, 1H), 5.13-5.07 (m, 2H), 3.63 (dt, J=6.0, 1.6, 2H).

Provenance & Evidence