1,9-Dibromononane

Chemical Properties

Uses

Synthesis

3937-56-2

4549-33-1

General procedure: In a dry reaction flask equipped with a stir bar, copper catalyst (2 mg, 0.002 mmol, 0.01 eq.), 1,9-nonanediol (0.20 mmol, 1.0 eq.), carbon tetrabromide (131.6 mg, 0.4 mmol, 2.0 eq.), and sodium bromide (41 mg, 0.40 mmol, 2.0 eq.) were added in sequence. The reaction vial was sealed and after displacing the air with nitrogen, anhydrous DMF (1.5 mL) was added via syringe. The reaction mixture was stirred under the light of a purple LED (394 nm) for 24 hours. Upon completion of the reaction, the mixture was transferred to a partitioning funnel and layered with ether (10 mL) and water (10 mL). The aqueous layer was separated and extracted with ether (2 x 10 mL). The organic layers were combined and washed sequentially with saturated aqueous NaHCO3 solution, Na2S2O3 solution and brine, dried with anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (100% hexane as eluent) to afford the target product 1,9-dibromononane.

References