1,3-Dibromopropane → (5-Bromo-2-methylpentane-2-sulfonyl)benzene

Participants

Reaction Conditions

Reaction Steps

A solution of n-butyllithium in cyclohexanes (1.82M, 18 ml, 32.8 mmol) was added dropwise to a stirred solution of phenyl i-propyl sulphone (5.55 g, 30.1 mmol) in tetrahydrofuran (60 ml) at −78° C. The mixture was stirred for 30 min. and 1,3-dibromopropane (6 ml, 58.7 mmol) was added via syringe over 30 seconds. The mixture was allowed to warm to 0° C. over 3 hours, then quenched with satd. aqueous NH4Cl and extracted into 1:1 mixture of i-hexane-diethyl ether. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified on silica (i-hexane-diethyl ether) to give the title product (5.7 g, 62%) as a white solid.

Provenance & Evidence