Diethyl Ether → 2-((3-(Bromomethyl)phenoxy)methyl)-7-chloroquinoline

Participants

Reaction Conditions

Reaction Steps

To the benzylic alcohol of Step 2 (47.0 g, 157 mmol) and CBr4 (60.08 g, 181 mmol) in CH2Cl2 (750 mL) at 0° C., a solution of 1,2-bis(diphenylphosphino) ethane (DIPHOS, 36.29 g, 91.1 mmol) in CH2Cl2 (350 mL) was added and the resulting mixture was stirred at 0° C. for 45 min. and at r.t. for 30 min. Ether was then added and the mixture was filtered through a pad of silica and the silica was washed with EtOAc:toluene 20:80 to yield 40.35 g (70%) of the pure title compound.

Provenance & Evidence