2-Bromo-1,1-dimethoxyethane → HCID 21071775, compound

Participants

Reaction Steps

To a solution of anhydrous ethanol (40 ml), sodium ethoxide (31.7 ml 21% wt., 86.94 mmol) and 2-bromo-5-methylphenol (Gewali, Mohan B.; Ronald, Bruce P. J. Org. Chem. 1980, 45, 2224–2229) (16.25 g, 86.94 mmol) was added 2-bromo-1,1-dimethoxy ethane (16.17 g, 95.64 mmol). The solution was heated to reflux overnight, reduced under vacuum and partitioned between water and ether. The aqueous layer was extracted with ether and the organics were passed through a silica plug and concentrated to afford 8.71 g (36%) of desired product as a pale yellow oil: 1H NMR (400 MHz, DMSO-d6): δ 2.19 (3H, s), 3.33 (6H, s), 3.96 (2H, d, J=5.1 Hz), 4.64 (1H, t, J=5.1 Hz), 6.98 (1H, d, J=8.5 Hz), 7.08 (1H, dd, J=8.4 Hz, 1.5 Hz), 7.35 (1H, d, J=1.7 Hz).

Provenance & Evidence