Sodium hydride → HCID 12548636, compound

Participants

Reaction Steps

To a solution of 27.4 g (685 mmol) of sodium hydride contained at 60% in mineral oil in dry dimethylformamide (425 ml) was added 42.4 g (227 mmol) of 4-bromobenzyl alcohol in an atmosphere of argon, and the mixture was allowed to react at 40-50° C. for 30 min. Then, 62.4 g (250 mmol) of 4-bromobenzyl bromide was added, and the mixture was reacted at room temperature for 15 hours. The reaction mixture was added to ice water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography for separation and purification. Elution with dichloromethane-hexane (1:1) yielded 72.7 g (204 mmol) of 4-bromobenzyl ether.

Provenance & Evidence