Sodium Carbonate → 7-Bromoisoquinoline-5-sulfonyl chloride

Participants

Reaction Steps

7-Bromo-isoquinoline (22.7 g, 109 mmol) is added to a stirred chlorosulfonic acid (230 mL) solution and the resultant mixture is heated at 150° C. under nitrogen for 22 hours. The solution is cooled to ambient temperature and poured very slowly into ice (2 Kg) cooled in a −10° C. bath. While cold, the mixture is adjusted to pH ˜10 with powered Na2CO3 (ca. 200 g) and 5N NaOH. The mixture is extracted with dichloromethane (1 L×2). The combined organic layers are dried over Na2SO4, filtered and concentrated in vacuo to give 16.3 g (crude yield 49%) of 7-bromo-isoquinoline-5-sulfonyl chloride as a tan solid.

Provenance & Evidence