Lithium Bromide → 5-[(2-bromoethyl)(2-chloroethyl)amino]-2,4-dinitrobenzamide

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Reaction Steps

A mixture of 2-[5-(aminocarbonyl)(2-chloroethyl)-2,4-dinitroanilino]ethyl methanesulfonate (5) [Friedlos et al., J. Med. Chem. 1997, 40, 1270] (0.91 g, 2.2 mmol) and LiBr (0.21 g, 2.4 mmol) in anhydrous MeCN (25 mL) was stirred under reflux for 1.5 h, then concentrated under reduced pressure. The residue was chromatographed on silica gel, eluting with CH2Cl2/EtOAc (3:2) to give a crude product contaminated with the corresponding dibromo mustard. Purification by multiple recrystallisations from EtOAc/I—Pr2O gave IIa2 (595 mg, 68%):

Provenance & Evidence