Iodine → 1-Chloro-7-iodoisoquinoline

Participants

Reaction Steps

To a stirred solution of 7-bromo-1-chloroisoquinoline (15 g, 62 mmol) in THF at −78° C., n-BuLi (123.7 mmol) was added. The resulting solution was stirred for 15 min. and, I2 (31.4 mg, 123.7 mmol) in THF was slowly added by syringe over a period of 5 min. The solution was then allowed to reach room temperature and treated with a saturated aqueous Na2S2O3 solution. The resulting mixture was extracted with diethyl ether (2×). The extracted organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuum. The residue was purified by flash chromatography to give the title compound.

Provenance & Evidence