1,3-Dibromopropane → HCID 67099665, compound

Participants

Reaction Steps

Ethyl 2-(4-chloro-2-iodophenyl)acetate (3.95 g, 12 mmol) was mixed in DMF (80 mL) in a round bottom flask. NaH (60% dispersion in mineral oil (0.54 g, 13 mmol)) was added, and the reaction mixture was stirred for 15 minutes under a nitrogen atmosphere. 1,3-dibromopropane (1.4 mL, 13 mmol, 1.1 eq) was added via syringe, and the reaction mixture was stirred for 2 hours. An additional 1.10 eq NaH (60% dispersion in mineral oil (0.54 g, 13 mmol)) was added, and the reaction was stirred for 3 hours. The reaction mixture was quenched with water and diluted with EtOAc. The organic layer was separated, washed with water and brine, dried (MgSO4), and concentrated in vacuo to give an orange oil. The crude product was purified by silica flash chromatography (0-30% DCM/hexane) to give the desired compound as a light yellow oil (2.01 g). MS (m/e)=365.1 (M+H)+.

Provenance & Evidence