Allyl bromide → HCID 59271856, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine (2.34 L, 16.4 mol) in THF (6 L) at −48° C. was added n-butyllithium (5.78 L, 14.5 mol) via additional funnel over 35 minutes, and the resulting mixture was warmed to −15° C. over 20 minutes, held at −15° C. for 10 minutes, then cooled down to −40° C. To this solution was added methyl 2-methoxypropionate (1.85 kg, 12.4 mol) via additional funnel over 1.75 hours. After stirring for 30 minutes, allyl bromide (1.4 L, 16.4 mol) was added via additional funnel. The resulting solution was stirred for 30 minutes, warmed to 0° C. over 1 hour, then quenched with 3NHCl (7 L), and extracted with MTBE (2×4 L). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was used in the next reaction without further purification.

Provenance & Evidence