Benzyl Bromide → HCID 86692160, compound

Participants

Reaction Conditions

Reaction Steps

Lithium bis(trimethysilyl)amide (4.8 mL, 4.8 mmol, 1 M in THF) was added to a solution of the tert-butyl 5-methoxy-1-oxoisoindoline-2-carboxylate (0.975 g) in THF (7 mL) at −78° C. After stirring the solution at −78° C. for 1 hr, benzyl bromide (0.88 mL, 7.41 mmol) was added, this was stirred at −78° C. for 1.5 hours. LC/MS showed complete conversion. Quenched the reaction mixture with saturated NaCl solution, then extracted with ethyl acetate, the combined organic layer was washed 1× with saturated NaCl solution. The organic phase was dried on Na2SO4 and the solvent was evaporated. The residue was purified by flash-chromatography on silica gel with 25-40% ethyl acetate in hexane, 0.92 g (2.59 mmol, 70%) of the product was obtained.

Provenance & Evidence