Ethanol → 2-(1-Methylcyclohexyl)-4-bromoanisole

Participants

Reaction Steps

To a suspension of 2-(1-methylcyclohexyl)-4-bromophenol (29.68 g, 0.110 mol) and K2CO3 (30.48 g, 0.221 mol) in 200 mL of anhydrous acetone was added a neat solution of dimethylsulfate (13.91 g, 0.110 mol) dropwise through a syringe over 5 minute at RT under argon. The resulting thick suspension was stirred over night at RT and 100 mL of EtOH was added. After 1 hour, the mixture was diluted with ether and water. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with water, brine and dried with MgSO4. After filtration, the solvents were removed and the residue distilled under reduced vacuum, 130–132° C. (0.7 mm/Hg). The impure fractions were combined and further purified on silica gel (hexane) to give a total amount of 2-(1-methylcyclohexyl)-4-bromoanisole as an oil (13.66 g, 44%). 1H NMR (300 MHz, CDCl3): δ 1.26 (s, 3H), 1.30–1.70 (m, 8H), 1.90–2.10 (m, 2H), 3.79 (s, 3H), 6.74 (d, J=8.4 Hz, 1H), 7.26 (dd, J1=8.4 Hz, J2=2.4 Hz, 1H), 7.36 (d, J=2.4 Hz, 1H).

Provenance & Evidence