Bromoacetyl bromide → 1-Vinyl pyrrolidone bromoacetate

Participants

Reaction Steps

A solution containing 330 mg of 1-vinyl pyrrolidone/vinyl alcohol copolymer (VI) in 8 mL of dry dimethyl formamide was taken in a two-neck round-bottomed flask and connected to nitrogen. The other neck was capped with a septum stopper. The flask was cooled in an ice bath. To the flask 0.25 mL of bromoacetyl bromide dissolved in 2 mL of DMF was added dropwise with a syringe through the septum stopper. The reaction was allowed to proceed at room temperature for 1 hour in the dark. The precipitation of the reaction mixture in 15-fold diethyl ether for 5 times yielded 270 mg of 1-vinyl pyrrolidone/bromoacetate copolymer (VII). A test of alkylating agents using 4-(p-nitrobenzyl)pyridine was positive indicating the presence of alkyl bromide in the copolymer (5). C-13 NMR (CD3OD) : 19.2, 27.4, 32.5, 33.7-37.1, 43.6-45.5, 48.2-48.9, 70.0-71.5, 168.6, 177.7. Elemental Analysis: found (Calcd): C, 40.05 (43.5); H, 4.87 (5.11); Br, 30.97 (28.94); N, 5.43 (5.07).

Provenance & Evidence