Water → 4-Bromo-1-[(2,2-dimethoxyethyl)oxy]-2-methylbenzene

Participants

Reaction Conditions

Reaction Steps

Bromoacetaldehyde dimethylacetal (6.05 ml) was added to a stirred solution of 4-bromo-2-methylphenol (10.0 g) and KOH (5.0 g) in dry DMSO (40 ml). The solution was warmed to 100° C. for 4 hours. After this time the reaction mixture was cooled to room temperature and poured into water (200 ml). The aqueous layer was extracted with ether (2×100 ml). The combined organic layers were separated, washed with 2N aqueous NaOH (2×50 ml), dried over MgSO4, filtered, and the solvent removed under reduced pressure to afford a brown oil. Purification by MPLC (15% ethyl acetate/n-hexane) afforded 4-bromo-1-[(2,2-dimethoxyethyl)oxy]-2-methylbenzene as a colourless oil (6.24 g). 1H NMR (360 MHz,CDCl3)δ2.21 (3H, s), 3.46 (6H,s), 3.98 (2H, d, J=3.6 Hz), 4.69 (1H, t, J=3.6 Hz), 6.56 (1H, d, J=7.2 Hz), 7.26 (1H, d, J=7.2 Hz), 7.39 (1H, s).

Provenance & Evidence