N-bromobutanimide → Phenol, 3-(bromomethyl)-4-chloro-, 1-methanesulfonate

Participants

Reaction Conditions

Reaction Steps

To a solution of the product from step A (61.3 g, 301 mmol) in 500 ml of carbon tetrachloride was added N-bromosuccinimide (80.3 g, 451 mmol) and 2,2-azobisisobutyronitrile (7.40 g, 45.0 mmol). The reaction was stirred at 80° C. for 2.5 hr, concentrated in vacuo, and then suspended in 30% EtOAc/Hexane (300 mL). The solution was filtered and concentrated to give crude product. The crude product was purified by silica gel chromatography (20% EtOAc/Hexane) to provide the title product as a yellow oil

Provenance & Evidence