Hydrochloric Acid → (1R,2S)-2-(4-Bromophenyl)cyclopropan-1-amine

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Reaction Steps

Zn dust (1.97 g, 30 mol) was added in small portions, over a period of 30 min, to a vigorously stirred solution of 1-bromo-4-[(trans)-2-nitrocyclopropyl]benzene (Intermediate A, 0.73 g, 3.0 mmol) in i-PrOH (25 mL) and HCl (11 mL of aqueous solution 2.7 N, 30 mmol). After 17 h the mixture was filtered through a pad of celite, that was washed with 10 mL of methanol. The filtrate was concentrated and 10 mL of water were added, washing with CH2Cl2 (3×15 mL). The organic layers were dried over anhydrous Na2SO4 and filtered. After removal of the solvent, the crude product was purified by column chromatography on silica gel (10% MeOH/CH2Cl2) affording 0.06 g of (trans)-2-(4-bromophenyl)cyclopropanamine [white solid. 10% yield].

Provenance & Evidence