1-Bromo-2-iodobenzene → 4-(4-Bromophenyl)pyridine

Participants

Reaction Steps

4-Bromopyridine hydrochloride is free based with saturated NaHCO3 solution and extracted into methylene chloride. The organic solution is concentrated at room temperature and used immediately without further purification. A portion of the solid obtained (3 g, 19 mmol) is treated as described in EXAMPLE 53, Part A with n-butyl lithium (14.25 mL of a 1.6 M solution in TIF, 22.8 mmol) and iodobromobenzene (5.39 g, 19 mmol). The crude product is purified by chromatography (30% EtOAc/hexanes to 60% EtOAc/hexanes) to obtain the title compound (2.59 g, 11.06 mmol).

Provenance & Evidence