Acetic Acid → (5-Bromo-3-indolylmethyl)-trimethylammonium Methyl Sulfate

Participants

Reaction Steps

According to the procedure of C. Huebner et al., J. Am. Chem. Soc., 75, 5887 (1953), a solution of 5-bromo-3-(dimethylaminomethyl)indole (28.3 g, 0.11 mol) and acetic acid (1.60 mL, 0.028 mol) in dry THF (154 mL) was added dropwise over a 1/2 hour period to a solution of dimethyl sulfate (52.04 mL, 0.55 mol) and acetic acid (1.60 mL, 0.028 mol) in dry THF (62 mL), keeping the temperature between 10°-15° C. The reaction was cooled in an ice bath for 1 hour, filtered, washed thoroughly with ether, and air dried for 1 hour to yield 41.6 g (100%) of product as a white solid. This was used immediately in the next step.

Provenance & Evidence