Bromine → HCID 178521543, compound

Participants

Reaction Conditions

Reaction Steps

(trans)-4-Phenylcyclohexanol (2 g) is dissolved in dichloromethane (40 mL) and cooled to −8° C. AlCl3 (3 g) is added portionwise and the mixture is stirred for further 15 minutes after addition is complete. Then a solution of bromine (1.87 mL) in dichloromethane (10 mL) is added dropwise. The mixture is stirred for 10 minutes and is then partitioned between dichloromethane and ice-water. Concentrated hydrochloric acid (20 mL) is added, the phases are separated and the aqueous phase is extracted 3 times with dichloromethane. The combined organic phases are dried (Na2SO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 2:1) to give the title compound. TLC: rf=0.3 (silicagel, cyclohexane/ethylacetate 2:1).

Provenance & Evidence