Bromine → HCID 18988172, compound

Participants

Reaction Steps

A solution of Br2 (1.0M) in glacial acetic acid (0.8 mL) was added to a solution of (RS)-2-(1-azabicyclo[2.2.2]oct-3-yl)-l(2H)-isoquinolinone (0.20 g; 0.787 mmol), from Example 2, in glacial acetic acid (5.0 mL). Thesolvent was removed under pressure and the residue was partitioned between methylene chloride (100 ml) and sodium carbonate (2.0M, 30 ml). The organic phase was separated and dried over anhydrous sodium sulfate. The mixture was then filtered and concentrated under reduced pressure. The solid residue was dissolved in ethyl alcohol (2 ml) and the solution acidified with hydrochloric acid (10%). A small amount of ethyl ether was added and crystals were collected and dried in vacuo to give (RS)-2-(1-azabicyclo[2.2.2]oct-3-yl)-4-bromo-1(2H)-isoquinolinone (0.0832 g, 0.248 mmol), m.p. 208°-209° C.

Provenance & Evidence