1-(Benzyloxy)-4-(bromomethyl)benzene → HCID 117778092, compound

Participants

Reaction Conditions

Reaction Steps

Di-tert-butyl N-trityl-L-glutamate (1.63 g, 3.25 mmol) was dissolved in tetrahydrofuran (12 ml) and the solution was cooled to −78° C. To the solution was added lithium 1,1,1,3,3,3-hexamethyldisilazide (1M in tetrahydrofuran, 7.14 ml) and, after stirring at −78° C. for 20 min, benzyl 4-(bromomethyl)phenyl ether (1.08 g, 3.90 mmol) in tetrahydrofuran (8 ml) was slowly added. The cooling bath was removed and the reaction mixture was stirred for 2 h. Then, 50 ml of 2 M aqueous hydrogen chloride solution were added and the mixture was extracted with dichloromethane. The organic phase was dried and concentrated under reduced pressure; the residue was purified by silica gel column chromatography to yield 813 mg (30%) of the product.

Provenance & Evidence