11-Bromoundecanoic acid → N3(CH2)10C(O)Cl

Participants

Reaction Steps

In a glass reaction vessel, 10.6 grams (40 mmol) of 11-Bromoundecanoic acid was dissolved in 225 milliliters DMF and 26 grams (400 mmol) sodium azide was added. The resulting stirred mixture was heated to 80° C. for 16h, and then the reaction mixture was worked up with ether and brine. The ether layer was dried (MgSO4), filtered, and concentrated to 9.5 grams of N3(CH2)10C(O)OH as a pale yellow oil which was used without purification. In a glass reaction vessel, the N3(CH2)10C(O)OH was dissolved in 120 milliliters benzene and 12.7 grams (100 mmol) oxalyl chloride was added. The reaction was allowed to stir for 20 h, at which time the volatiles were removed in vacuo. The resulting residue was dissolved in pentane and filtered in a nitrogen atmosphere to remove solids. Concentration of the filtrate afforded N3(CH2)10C(O)Cl as a clear, yellow oil.

Provenance & Evidence