Diisopropylamine → Methyl 5-bromo-2-methyl-2-phenyl-pentanecarboxylate

Participants

Reaction Conditions

Reaction Steps

15 g (0.234 mol) of n-butyl lithium as a 2.5 molar solution in hexane are added dropwise to a solution of 32.8 ml (0.234 mol) of diisopropylamine in 200 ml of anhydrous tetrahydrofuran at −30° C. and stirred for 10 minutes at −10° C. 38.4 g (0.234 mol) of methyl 2-phenylpropionate are added dropwise at −76° C. and stirred for 30 minutes at this temperature. Then 26.3 ml (0.257 mol) of 1,3-dibromopropane are added, when the addition has ended the cooling bath is removed and the mixture is stirred for 14 hours at ambient temperature. The reaction solution is poured onto 1.2 l of water and extracted with diethylether. The organic phases are extracted with water, dried over sodium sulphate and the solvent is removed. The residue is distilled under high vacuum.

Provenance & Evidence