Carbon tetrabromide → 2-(2-Bromoethyl)-1-chloro-3-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(2-chloro-6-nitrophenyl)ethanol (33.0 g, 0.16 mole) in methylene chloride (500 mL) was added triphenylphosphine (43.0 g, 0.16 mole) and the mixture was cooled to 0° C. Carbon tetrabromide (54.4 g, 0.16 mole) in methylene chloride (100 mL) was added dropwise through an addition funnel. The reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue purified by flash column chromatography (silica gel, ethyl acetate:hexanes 1:9) to provide 39.0 g of the title compound as a yellow solid. 1H NMR (CDCl3): 7.70 δ (d, 1H); 7.60 δ (d, 1H); 7.35 δ (t, 1H); 3.60 δ (t, 2H); 3.45 δ (t, 2H).

Provenance & Evidence