Ethyl bromoacetate → HCID 62047227, compound

Participants

Reaction Steps

To a 250 mL round bottom flask equipped with a stir bar was added 6-bromoindole (5 g; 25.5 mmol) and THF (50 mL). To this stirred solution, under argon, was added sodium bis(trimethylsilyl)amide (1M in tetrahydrofuran)(51 mL; 51 mmol). The resulting brown solution was stirred at room temperature for 1 h. At this point the mixture was cooled to −5° C., and a solution of ethyl bromoacetate (5.6 mL; 51 mmol) in THF (4 mL) added. The resulting brownish yellow precipitate was warmed to room temperature and further stirred for 1 h. The reaction mixture was diluted with ethyl acetate (100 mL) and the organic phase successively washed with water (3×50 mL) and brine (100 mL). The organic phase was separated, dried (sodium sulphate) and the solvent removed in vacuo to yield the title compound as a brown oil (crude weight: 7.3 g). 13C NMR (CDCl3): δ168.3, 137.4, 129.4, 123.2, 122.4, 115.6, 112.2, 102.7, 61.7, 47.7, 14.2.

Provenance & Evidence