N-bromobutanimide → HCID 18451498, compound

Participants

Reaction Steps

2-Chloro-5-cyclopropyl-6-fluoroaniline (9.4 g, 50.6 mmol) and N-bromosuccinimide (9.4 g, 52.8 mmol) are dissolved with stirring in 100 mL of anhydrous DMF. The reaction mixture is stirred overnight and then most of the DMF is removed by rotary evaporator under high vacuum. The residue is partitioned between 1:1 Et2O/hexane (500 mL) and water (500 mL). The organic layer is washed with brine (3×250 mL), dried (MgSO4) and concentrated by rotary evaporator. The crude material is purified using flash chromatography (7% CH2Cl2/hexanes) to give 2-chloro-4-bromo-5-cyclopropyl-6-fluoroaniline as a light orange oil.

Provenance & Evidence