2-bromo-5-methylphenol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Analogously to Method F, 10.0 g of 2-bromo-5-methylphenol and 11.6 g of 1-chloro-3-methoxypropane are reacted. The title compound is obtained as a slightly orange oil. Rf=0.31 (1:4 EtOAc-heptane); Rt=5.01.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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). The solution was heated to reflux overnight partitioned between water and ether The aqueous layer was extracted with ether concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Analogously to Method F, 10.0 g of 2-bromo-5-methylphenol and 11.6 g of 1-chloro-3-methoxypropane are reacted. The title compound is obtained as a slightly orange oil. Rf=0.31 (1:4 EtOAc-heptane); Rt=5.01.